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Studies on the amination of aryl chlorides with a monoligated palladium catalyst: Kinetic evidence for a cooperative mechanism
Combined spectroscopic, crystallographic, and kinetic studies of the mechanism of aromatic amination with the efficient dinuclear Pd precatalyst [Pd2Cl(μ-Cl)PtBu2(Bph-Me)] (Bph-Me=2′-methyl-[1, 1'-biphenyl]-2-yl) have revealed overlapping, yet cooperative, mechanistic scenarios, the relative weights of which are strongly influenced by the products formed as the reaction proceeds. The stability and evolution of the precatalyst in solution has been studied and several metalation pathways that point to a single monoligated intermediate have been identified. Our work sheds light on the nature of the catalytic species involved in the process and on the structure of the corresponding catalytic network. Two cycles for catalytic amination: Combined spectroscopic, crystallographic, and kinetic studies on the amination of p-chlorotoluene with p-toluidine with a monoligated Pd catalyst have revealed overlapping, yet cooperative, mechanistic scenarios, the relative weights of which are strongly influenced by the products formed as the reaction proceeds (see scheme; L=2′-methyl-[1,1'-biphenyl]-2-yl).
Jimeno, Ciril,Christmann, Ute,Escudero-Adan, Eduardo C.,Vilar, Ramon,Pericas, Miquel A.
p. 16510 - 16516
(2012)
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Electron Transfer Rate Maxima at Large Donor-Acceptor Distances
Because of their low mass, electrons can transfer rapidly over long (>15 ?) distances, but usually reaction rates decrease with increasing donor-acceptor distance. We report here on electron transfer rate maxima at donor-acceptor separations of 30.6 ?, observed for thermal electron transfer between an anthraquinone radical anion and a triarylamine radical cation in three homologous series of rigid-rod-like donor-photosensitizer-acceptor triads with p-xylene bridges. Our experimental observations can be explained by a weak distance dependence of electronic donor-acceptor coupling combined with a strong increase of the (outer-sphere) reorganization energy with increasing distance, as predicted by electron transfer theory more than 30 years ago. The observed effect has important consequences for light-to-chemical energy conversion.
Kuss-Petermann, Martin,Wenger, Oliver S.
p. 1349 - 1358
(2016)
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Improved Buchwald-Hartwig Amination by the Use of Lipids and Lipid Impurities
The development of green Buchwald-Hartwig aminations has long been considered challenging, due to the high sensitivity of the reaction to the environment. Here we show that food-grade and waste vegetable oils, triglycerides originating from animals, and natural waxes can serve as excellent green solvents for Buchwald-Hartwig amination. We further demonstrate that amphiphiles and trace ingredients present in triglycerides as additives have a decisive effect on the yields of Buchwald-Hartwig aminations.
Bayer, Annette,Gevorgyan, Ashot,Hopmann, Kathrin H.
supporting information

(2021/11/12)

Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles
A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated, giving the desired coupling products in good to excellent yields (62–94%). The method is practical and offers an alternative to the corresponding copper-catalyzed Chan-Evans-Lam process for the construction of C–N bonds.
Zhang, Maoyuan,Xu, Zengbing,Shi, Dabin
(2020/12/25)

Mechanochemical synthesis of aromatic sulfonamides
A three-component Pd-catalysed aminosulfonylation reaction of K2S2O5 and amine with aryl bromides or aromatic carboxylic acids was developed. This strategy was developed to utilise mechanical energy and accommodate primary as well as secondary aliphatic and aromatic amines to provide a new shortcut to a wide range of sulfonamides. Studies on the scope and limitations of the reaction indicated its tolerance of a vast range of functional groups and many structural patterns. The reactions were scaled up to gram quantities.
Iaroshenko, Viktor O.,Mkrtchyan, Satenik
supporting information
p. 11029 - 11032
(2021/11/03)

Temperature-Dependent Effects of Alkyl Substitution on Diarylamine Antioxidant Reactivity
Alkylated diphenylamines are among the most efficacious radical-trapping antioxidants (RTAs) for applications at elevated temperatures since they are able to trap multiple radical equivalents due to catalytic cycles involving persistent diphenylnitroxide and diphenylaminyl radical intermediates. We have previously shown that some heterocyclic diarylamine RTAs possess markedly greater efficacy than typical alkylated diphenylamines, and herein, report on our efforts to identify optimal alkyl substitution of the scaffold, which we had found to be the ideal compromise between reactivity and stability. Interestingly, the structure-activity relationships differ dramatically with temperature: para-alkyl substitution slightly increased reactivity and stoichiometry at 37 and 100 °C due to more favorable (stereo)electronic effects and corresponding diarylaminyl/diarylnitroxide formation, while ortho-alkyl substitution slightly decreased both reactivity and stoichiometry. No such trends were evident at 160 °C; instead, the compounds were segregated into two groups based on the presence/absence of benzylic C-H bonds. Electron spin resonance spectroscopy indicates that increased efficacy was associated with lesser diarylnitroxide formation, and deuterium-labeling suggests that this is due to abstraction of the benzylic H atom, precluding nitroxide formation. Computations predict that this reaction path is competitive with established fates of the diarylaminyl radical, thereby minimizing the formation of off-cycle products and leading to significant gains in high-temperature RTA efficacy.
Shah, Ron,Poon, Jia-Fei,Haidasz, Evan A.,Pratt, Derek A.
p. 6538 - 6550
(2021/05/29)

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids
The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.
Wang, Dan,Wan, Zhaohua,Zhang, Heng,Alhumade, Hesham,Yi, Hong,Lei, Aiwen
p. 5399 - 5404
(2021/10/20)

Selective primary aniline synthesis through supported Pd-catalyzed acceptorless dehydrogenative aromatization by utilizing hydrazine
By utilizing hydrazine (N2H4) as the nitrogen source in the presence of a hydroxyapatite-supported Pd nanoparticle catalyst (Pd/HAP), various primary anilines can be selectively synthesized from cyclohexanonesviaacceptorless dehydrogenative aromatization. The strong nucleophilicity of N2H4and the stability of the hydrazone intermediates can effectively suppress the formation of the undesired secondary aniline byproducts.
Lin, Wei-Chen,Yamaguchi, Kazuya,Yatabe, Takafumi
supporting information
p. 6530 - 6533
(2021/07/07)

Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
p. 403 - 413
(2020/12/23)

Diaromatic ring amide compound and application thereof
The invention relates to a diarylcyclic amide compound and application thereof. According to the invention, a high-purity solid can be obtained mainly by using the traditional recrystallization and column separation, the solid can be converted into corresponding diarylamine at high yield, especially high-purity liquid diarylcyclic secondary amine can be easily and conveniently obtained, and a high-purity organic semiconductor can be produced by the high-purity secondary amine on a large scale, and can be used in OPV or OLED devices. The chemical formula of the compound is shown in the specification, wherein R1 and R2 are H, D, F, or alkyl, alkoxy, fluoroalkyl, silyl, cycloalkyl, cycloalkoxy,-CN, -NO2 or phenyl with the carbon atom number smaller than 12; the dotted line is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom, a carbon atom or a chemical bond for connecting two benzene rings or is nothing at all; and z is a protecting group and is selected from carbobenzoxy, t-butyloxycarbonyl, fluorene methoxycarbonyl, allyloxycarbonyl, trimethylsilylethoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, phthaloyl, p-toluenesulfonyl, trifluoroacetyl, benzoyl, trityl, 2, 4-dimethoxybenzyl, p-methoxybenzyl and benzyl.
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Paragraph 0101; 0102; 0104-0106

(2021/07/01)

Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)–Olefin Precatalyst
We report that Ni(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature. Due to its apparent stability, use of Ni(COD)(DQ) as a precatalyst allows reactions to be conveniently performed without use of an inert-atmosphere glovebox, as demonstrated across several case studies.
Apolinar, Omar,Derosa, Joseph,Eastgate, Martin D.,Engle, Keary M.,Joannou, Matthew V.,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
supporting information
p. 7409 - 7413
(2020/04/10)

Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle
In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).
Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri
p. 3010 - 3021
(2020/04/29)

Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation
Reaction of 1,4-diazabutadiene (p-RC6H4N = C(H)(H)C = NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) with CuCl2·2H2O in methanol at ambient temperature (25 °C) affords a group of doubly chloro-bridged dicopper complexes of type [{CuI(L-R)Cl}2], designated as 1-R. Similar reaction carried out in acetonitrile furnishes a family of doubly chloro-bridged dicopper complexes of type [{CuII(L-R)Cl2}2], designated as 2-R. Molecular structures of 1-OCH3 and 2-OCH3 have been determined by X-ray crystallography. While copper(I) is having a nearly tetrahedral N2Cl2 coordination sphere in 1-OCH3, the N2Cl3 coordination sphere around copper(II) is distorted square pyramidal in nature in 2-OCH3. Isolated 2-R complexes, on dissolution in methanol, are found to undergo facile reduction of the metal center to generate the corresponding 1-R complexes. The 1-R and 2-R complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the 1-R and 2-R complexes shows both metal-centered and ligand centered redox responses. The 1-R complexes are found to efficiently catalyze C-N cross-coupling reactions between arylboronic acids and aryl amines; while the 2-R complexes display notable catalytic efficiency for nitroaldol reactions.
Mukherjee, Aparajita,Basu, Semanti,Bhattacharya, Samaresh
(2019/11/11)

Ir-Catalyzed C-H Amidation Using Carbamoyl Azides for the Syntheses of Unsymmetrical Ureas
An iridium-catalyzed C-H amidation for the syntheses of unsymmetrical urea was developed using carbamoyl azides (R(R′)N-C(O)-N3) as the nitrogen source. A combination of iridium and silver gave an active catalyst for C-N bond formation. A variety of urea derivatives were synthesized using carbamoyl azides with only dinitrogen byproducts. Finally, the use of the transient directing group strategy with carbamoyl azides extended the substrate scope of the catalytic C-H amidation to yield aldehyde-containing unsymmetrical ureas.
Yoo, Kwangho,Lee, Jooyeon,Park, Myung Hwan,Kim, Youngjo,Kim, Hyun Jin,Kim, Min
p. 6233 - 6241
(2020/05/22)

Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
supporting information
p. 8086 - 8090
(2020/11/03)

Activator-Promoted Aryl Halide-Dependent Chemoselective Buchwald-Hartwig and Suzuki-Miyaura Type Cross-Coupling Reactions
Herein, we report the development of aryl halide-dependent chemoselective reactions, viz., the Buchwald-Hartwig type coupling reaction of an aryl iodide with an arylboronic acid and an aryl amine in the presence of a heterogeneous and reusable nickel catalyst and the Suzuki-Miyaura type coupling of an aryl chloride under similar conditions. Control experiments revealed that the presence of stoichiometric amounts of the phenylboronic acid/ester and aryl amine are essential for both reactions. NMR and XAFS studies suggested the formation of a boron-amine "ate"complex.
Dhital, Raghu N.,Hashizume, Daisuke,Hu, Hao,Ishii, Rikako,Sato, Takuma,Sen, Abhijit,Takaya, Hikaru,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
(2020/06/29)

One-pot synthesis of symmetrical and asymmetrical diphenylamines from guanidines with aryl iodide using Cu/Cu2O nanocatalyst
This work reports the selective one-pot synthesis of symmetrical and asymmetrical amines from guanidines as ammonia surrogate. The use of guanidine as ammonia source will eliminate the need of handling liquid ammonia. The reaction was performed using Cu/Cu2O nanocatalyst under ligand-free condition. The synthesized catalyst was characterized by a various technique like XRD, FEG-SEM, HRTEM and XPS. The different diphenylamines are produced in good to very good yields. Recyclability study of catalyst shows that up to five cycles there is no significant loss in its activity.
Chaurasia, Shivkumar R.,Bhanage
(2020/06/01)

N-Heterocyclic Olefin-Ligated Palladium(II) Complexes as Pre-Catalysts for Buchwald–Hartwig Aminations
New N-heterocyclic olefins (NHOs) are described with functionalization on the ligand heterocyclic backbone and terminal alkylidene positions. Various PdII–NHO complexes have been formed and their use as pre-catalysts in Buchwald–Hartwig aminations was explored. The most active system for catalytic C?N bond formation between hindered arylamine and arylhalide substrates was accessed by combining a backbone methylated NHO with [Pd(cinnamyl)Cl]2 in the presence of NaOtBu as a base. In these active systems evidence suggests that catalysis is mediated by colloidal palladium metal, highlighting a different coordination ability of NHOs in comparison with commonly used N-heterocyclic carbene co-ligands.
Watson, Ian C.,Schumann, André,Yu, Haoyang,Davy, Emma C.,McDonald, Robert,Ferguson, Michael J.,Hering-Junghans, Christian,Rivard, Eric
supporting information
p. 9678 - 9690
(2019/07/09)

New compounds and organic light-emitting diode including the same
PURPOSE: A fused aryl compound is provided to be stable and to have excellent luminous efficiency, thereby capable of providing an organic electroluminescence device with excellent driving voltage, external quantum efficiency, color purity and life time performance. CONSTITUTION: A fused aryl compound is represented by chemical formula 1. In chemical formula 1, each of R is selected from hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C7-30, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstituted C5-30 arylthioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide, and ester.
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Paragraph 0161-0167

(2019/08/30)

Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium
Arylamines are commercially and synthetically useful compounds with a wide variety of applications. Their preparation has been traditionally achieved using metal-catalyzed C?N coupling reactions with aryl halides. In this work, 17 different diarylamines are prepared from phenols by using ammonium formate as the aminating reagent. Phenolic compounds are more desirable feedstocks, owing to their availability from lignin, making them valuable biorenewable alternatives to aryl halides. Ammonium formate is found to be a convenient surrogate for ammonia and a useful aminating reagent for phenols. Diarylamine products are obtained in good to excellent yields while only water and CO2 are generated as byproducts of the transformation.
Dominguez-Huerta, Alejandra,Perepichka, Inna,Li, Chao-Jun
p. 2999 - 3002
(2019/06/13)

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines
The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.
Chen, Kai,Chen, Wanzhi,Chen, Wei,Liu, Miaochang,Wu, Huayue
p. 8110 - 8115
(2019/08/26)

Copper-Catalyzed NaBAr 4-Based N-Arylation of Amines
Using NaBAr 4 as an arylating agent, the formation of carbon-heteroatom bonds by a Cham-Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr 4 proceeds smoothly to offer the corresponding products in good to excellent yields.
Yang, Qin,Lei, Xiaoli,Yin, Zhijian,Deng, Zhihong,Peng, Yiyuan
supporting information
p. 538 - 544
(2019/01/10)

Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning
A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), was synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regard to the electron push-pull substituent effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, a different charge-transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron-withdrawing group of CN-substituted 2a did not correlate with the other R group compounds. From the experimental data and density functional theory calculations, we assume that there is a constraint on emission color tuning to generate higher energy of blue emission in the D-A-D molecular system, due to the reverse charge-transfer property caused by the strong electron-withdrawing group.
Ahn, Mina,Kim, Min-Ji,Wee, Kyung-Ryang
p. 12050 - 12057
(2019/10/11)

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane
The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.
Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue
p. 3874 - 3878
(2019/08/07)

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
Mohammadinezhad, Arezou,Akhlaghinia, Batool
supporting information
p. 15525 - 15538
(2019/10/19)

Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
p. 4891 - 4900
(2018/11/21)

Immobilization of nickel ions onto the magnetic nanocomposite based on cross-linked melamine groups: Effective heterogeneous catalyst for N-Arylation of Arylboronic acids
A new magnetic heterogeneous catalyst was synthesized by immobilization of nickel ions onto a cross-linked polymeric nanocomposite composed of cyanuric chloride, ethylenediamine and functionalized magnetic nanoparticles. The resulting nitrogen rich support was capable of adsorbing large amounts of nickel ions (1.20 mmol g?1). The synthesized catalyst was characterized using AAS, TEM, FT-IR, EDX, TGA, SEM, BET and XRD techniques. The performance of the prepared catalyst was investigated in the C-N coupling of arylamines with aryl boronic acids. The reaction was carried out under a mild condition and good to moderate to good yields of products was obtained using only 5.0 mol% of the catalyst. The catalyst was easily recovered and reused for at least 7 times without any significant loss of its activity.
Pourjavadi, Ali,Keshavarzi, Nahid,Moghaddam, Firouz Matloubi,Hosseini, Seyed Hassan
(2017/10/23)

PREPARATION OF SECONDARY AMINES WITH ELECTROPHILIC N-LINCHPIN REAGENTS
In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identifical groups. Also provided herein are compositions for use in the preparation of the secondary amine.
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Page/Page column 101-102

(2018/12/13)

A green and mild procedure to selective synthesis of diarylamine via domino reaction of aryl halides and arginine catalyzed by magnetic-MOF
Efficient and selective direct synthesis of diarylamines from aryl halides and arginine as a nitrogen-donor reagent is reported. Arginine, which is an oral supplement, acts as a useful nitrogen source donor in the copper-catalyzed reaction. Fe3O4/Cu3(BTC)2, which was easily separated and recycled with a magnet, improved the rate and facilitation of the synthesis of diarylamines selectively. The introduction of a new and available N-source, simple magnetic separation process, normal atmospheric conditions, and excellent yields under mild reaction conditions are other important features of this work.
Soleiman-Beigi, Mohammad,Mohammadi, Fariba
(2019/01/03)

[Pd(IPr*R)(acac)Cl]: Efficient bulky Pd-NHC catalyst for Buchwald-Hartwig C-N cross-coupling reaction
A series of bulky palladium catalysts based on N-heterocyclic carbene, (Pd(NHC)(acac)Cl: NHC = IPr*me = N,N′-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2 -ylidene, Pd(IPr*me)(acac)Cl; NHC = IPr*ipr = N,N′-bis(2,6-bis(di-4-isopropylphenyl)-4-methylphenyl)-imidazol-2 -ylidene, Pd(IPr*ipr)(acac)Cl; and NHC = IPr*tBu = N,N′-bis(2,6-bis(di-4-(tert-butyl)phenyl)- 4-methylphenyl)- imidazol-2-ylidene, Pd(IPr*tBu)(acac)Cl; acac = acetylacetonate), have been designed and synthesized. These three new catalysts showed much better catalytic activity in the Buchwald?Hartwig arylamination coupling reaction as compare to the earlier congener (IPr*)Pd(acac)Cl (IPr* = N,N′-bis(2,6-diphenylmethyl)-4-methylphenylimidazol-2-ylidene). The highly active PdII precatalyst [Pd(IPr*me)(acac)Cl] has been fully explored by using a wide range of substrates with different electronic and steric demands of coupling partners, for which up to 99% isolated yields were obtained. Remarkably, the moderate isolated yield was obtained for the challenging coupling of the amine bearing very bulky groups.
Tian, Xiabing,Lin, Jing,Zou, Sheng,Lv, Junwei,Huang, Qingfei,Zhu, Jin,Huang, Shuping,Wang, Qiwei
supporting information
p. 125 - 130
(2018/03/06)

Palladium-catalyzed amination of aryl sulfoxides
Amination of diaryl sulfoxides with anilines and alkylamines has been accomplished under palladium/N-heterocyclic carbene (NHC) catalysis. Owing to its electron deficiency, the leaving arenesulfenate anion would be smoothly released from the palladium center to result in uneventful catalyst turnover under milder reaction conditions in comparison with previous C-S bond amination reactions. This amination accommodated a wider range of functional groups such as silyl, boryl, methylsulfanyl, and halogen moieties. Regioselective amination of unsymmetrical diaryl sulfoxides was also executed by means of steric bias.
Yoshida, Yuto,Otsuka, Shinya,Nogi, Keisuke,Yorimitsu, Hideki
supporting information
p. 1134 - 1137
(2018/02/23)

Formal arylation of NH3 to produce diphenylamines over supported Pd catalysts
In the presence of supported Pd nanoparticle catalysts, e.g., Pd/Al2O3, various diphenylamines could be synthesized through acceptorless formal arylation using NH3 or its surrogates, e.g., urea, as nitrogen sources and cyclohexanones as arylation sources. The observed catalysis was truly heterogeneous, and the catalyst was reusable with retention of its high catalytic performance.
Koizumi, Yu,Taniguchi, Kento,Jin, Xiongjie,Yamaguchi, Kazuya,Nozaki, Kyoko,Mizuno, Noritaka
supporting information
p. 10827 - 10830
(2017/10/09)

Pyridazines derivative, and preparation method and application thereof
The invention provides a pyridazines derivative, and a preparation method and application thereof, and relates to the technical field of organic photoelectric materials. By optimizing the molecular structure design, the obtained pyridazines derivative has good hole transmission capability, and can be used for preparing organic electroluminescence devices; particularly, the pyridazines derivative shows the advantages of high efficiency, high brightness and long service life when being used as a hole transmission material in the organic electroluminescence device. The performance is better than that of the existing common use OLED (optical light emitting diode) device. The invention also provides the preparation method of the pyridazines derivative. The preparation method has the advantages that the method is simple; raw materials can be easily obtained.
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Paragraph 0051; 0054; 0056-0057; 0061

(2017/04/28)

Catalytic Asymmetric Chlorocyclization of 2-Vinylphenylcarbamates for Synthesis of 1,4-Dihydro-2H-3,1-benzoxazin-2-one Derivatives
A facile synthetic approach to a series of chiral 4-chloromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives has been described. This transformation is achieved through the catalytic asymmetric chlorocyclization of 2-vinylphenylcarbamates using a newly developed organocatalyst. Furthermore, the resulting products can be easily converted into diverse bioactive agents.
Yu, Yan-Min,Huang, Ya-Nan,Deng, Jun
supporting information
p. 1224 - 1227
(2017/03/14)

N/O-doped carbon as a "solid ligand" for nano-Pd catalyzed biphenyl- and triphenylamine syntheses
A series of N/O-doped porous carbon supported nanopalladium catalysts have been successfully prepared, in which the N/O doped carbons were controllably produced via polypyrrole/furan synthesis followed by carbonization. These catalysts exhibit good performance in biphenylamine and triphenylamine syntheses with nitrobenzene and cyclohexanone as starting materials. Their catalytic activity can be tuned efficiently by the N/O functional groups on the carbon surface. TEM, XRD, XPS and laser Raman methods were applied to probe the structure of these catalysts. These results indicate that the Pd nanoparticles were supported on N/O-doped porous carbon via the "coordination" between Pd nanoparticles and N/O functional groups including O-CO, CN and tertiary nitrogen, and better catalytic performance was obtained if carbon with the highest N-species loading was used as the support. In addition, a mechanistic study proved that the reaction starts with the catalytic reduction of nitrobenzene with cyclohexanone as the hydrogen source. During this reaction, aniline was formed and the cyclohexanone was transformed into phenol. Then biphenylamine and triphenylamine were generated through the reaction of aniline and cyclohexanone. This work should facilitate the controllable preparation of carbon supported nanocatalysts with specific activity, and open up a promising pathway for the development of new methodologies for N-containing fine chemical synthesis.
Pang, Shaofeng,Zhang, Yujing,Huang, Yongji,Yuan, Hangkong,Shi, Feng
p. 2170 - 2182
(2017/07/24)

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.
Guan, Changwei,Feng, Yuanyuan,Zou, Gang,Tang, Jie
p. 6906 - 6913
(2017/11/03)

Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation
Given the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chemistry. Here, we present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of symmetrical and unsymmetrical diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C-N cross-coupling methods that are currently used to access structurally diverse secondary amines.
Kattamuri, Padmanabha V.,Yin, Jun,Siriwongsup, Surached,Kwon, Doo-Hyun,Ess, Daniel H.,Li, Qun,Li, Guigen,Yousufuddin, Muhammed,Richardson, Paul F.,Sutton, Scott C.,Kürti, László
supporting information
p. 11184 - 11196
(2017/08/21)

Arylation of aniline and amines by Pd-(N-Heterocyclic carbene) complexes
Aminoarenes constitute valuable building blocks in organic synthesis and an essential skeleton ubiquitously found in ligands, agrochemicals, and pharmaceuticals. This synopsis presents recent amination methods using nitrogen-heteroatom bonds as a powerful and versatile platform to rapidly synthesize diverse aminoarenes, with transition-metal catalyzed arene C-H amination. The Buchwald-Hartwig amination has been investigated theoretically and experimentally to examine the scope of possible bases under different reaction conditions. We report examples of the palladium NHC (N-heterocyclic carbene) catalyzed amination of aryl halides with anilines and amines in the presence of dimethoxyethane solvent and potassium tertiary-butoxide as a base.
?ahin, Neslihan,Dü?ünceli, Serpil Demir,?zdemir, ?smail
p. 1506 - 1517
(2017/08/02)

Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles
Diarylamines are an important class of widely utilized chemicals, and development of diverse procedures for their synthesis is of great importance. Herein, we have successfully developed novel versatile catalytic procedures for the synthesis of diarylamines through acceptorless dehydrogenative aromatization. In the presence of a gold-palladium alloy nanoparticle catalyst (Au-Pd/TiO2), various symmetrically substituted diarylamines could be synthesized starting from cyclohexylamines. The observed catalysis of Au-Pd/TiO2 was heterogeneous in nature and Au-Pd/TiO2 could be reused several times without severe loss of catalytic performance. This transformation needs no oxidants and generates molecular hydrogen (three equivalents with respect to cyclohexylamines) and ammonia as the side products. These features highlight the environmentally benign nature of the present transformation. Furthermore, in the presence of Au-Pd/TiO2, various kinds of structurally diverse unsymmetrically substituted diarylamines could successfully be synthesized starting from various combinations of substrates such as (i) anilines and cyclohexanones, (ii) cyclohexylamines and cyclohexanones, and (iii) nitrobenzenes and cyclohexanols. The role of the catalyst and the reaction pathways were investigated in detail for the transformation of cyclohexylamines. The catalytic performance was strongly influenced by the nature of the catalyst. In the presence of a supported gold nanoparticle catalyst (Au/TiO2), the desired diarylamines were hardly produced. Although a supported palladium nanoparticle catalyst (Pd/TiO2) gave the desired diarylamines, the catalytic activity was inferior to that of Au-Pd/TiO2. Moreover, the activity of Au-Pd/TiO2 was superior to that of a physical mixture of Au/TiO2 and Pd/TiO2. The present Au-Pd/TiO2-catalyzed transformation of cyclohexylamines proceeds through complex pathways comprising amine dehydrogenation, imine disproportionation, and condensation reactions. The amine dehydrogenation and imine disproportionation reactions are effectively promoted by palladium (not by gold), and the intrinsic catalytic performance of palladium is significantly improved by alloying with gold. One possible explanation of the alloying effect is the formation of electron-poor palladium species that can effectively promote the β-H elimination step in the rate-limiting amine dehydrogenation.
Taniguchi, Kento,Jin, Xiongjie,Yamaguchi, Kazuya,Nozaki, Kyoko,Mizuno, Noritaka
p. 2131 - 2142
(2017/03/09)

The 4.4′-benzidine rearrangement of 4-alkyl substituted hydrazobenzenes
When treated with dilute inorganic acids N,N′-diarylhydrazines (hydrazobenzenes) with an alkyl substituent in the 4-position undergo [5,5]-sigmatropic rearrangement reactions to furnish 4-(4′-aminophenyl)-4-alkylcyclohexa-2,5-dienimines (ipso-benzidines) in moderate to excellent yields. Steric bulk of the 4-alkyl substituent in the starting material decreases the yield of the respective ipso-benzidine. Additional electron-donating alkyl substituents in the ortho- and/or meta-positions on both rings generally promote the reaction and consequently increase the yield of the 4.4′-benzidine rearrangement product. Described herein are our findings regarding the scope and limits of this unusual benzidine rearrangement.
Bouillon, Marc E.,Meyer, Hartmut H.
supporting information
p. 3151 - 3161
(2016/05/24)

Synthesizing method of 4,4'-dimethyltriphenylamine and production system
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesizing method of 4,4'-dimethyltriphenylamine and a production system .The method includes the steps that paratoluidine is hydrolyzed through a catalyst under the acid condition to prepare p-cresol, and p-cresol reacts with paratoluidine to prepare 4,4'-dimethyltriphenylamine .The method has the advantages that the method is simple in process, mild in reaction condition, safe and reliable in production process, low in production cost, small in by-product and small in sewage amount, and raw materials are easy to obtain.
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Paragraph 0007; 0027; 0028; 0032-0038

(2018/02/04)

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides
A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.
Oderinde, Martins S.,Jones, Natalie H.,Juneau, Antoine,Frenette, Mathieu,Aquila, Brian,Tentarelli, Sharon,Robbins, Daniel W.,Johannes, Jeffrey W.
supporting information
p. 13219 - 13223
(2016/10/30)

Exploring the Catalytic Reactivity of Nickel Phosphine-Phosphite Complexes
In this study, we present an investigation into various nickel phosphite and phosphite-phosphine complexes for use in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions and the ammonia arylation reaction. In these coupling reactions, it was discovered that the Ni[P(OEt)3]4, (dppf)Ni[P(OPh)3]2, and (binap)Ni[P(OPh)3]2 catalysts were the most effective. In addition, an optimisation process for these catalytic systems as well as functional group compatibility are discussed.
Kampmann, Sven S.,Man, Nikki Y. T.,McKinley, Allan J.,Koutsantonis, George A.,Stewart, Scott G.
p. 1842 - 1853
(2015/12/26)

Copper mediated formation of carbon-heteroatom bonds using organoboron reagents and ultrasound
This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%.1 Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.
Musolino, Bryan J.,Kabalka, George W.
p. 271 - 297
(2015/03/04)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode and comprising the compound, the element showing improved luminescence efficiency, stability, and life span.
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Paragraph 0349 - 0352; 0392; 0393

(2016/10/07)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
Disclosed is a compound presented by chemical formula 1. Disclosed is an organic electronic element including a first electrode, a second electrode, and an organic substance layer located between the first electrode and the second electrode, wherein the organic substance layer includes the compound presented by chemical formula 1. When the compound represented by chemical formula 1, light emitting efficiency, stability, and life of the organic electronic element can be improved.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transporting layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transporting layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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Paragraph 0347; 0380; 0381

(2016/10/08)

Hole Transport Materials with High Triplet Energy for Long Lifespan OLED and OLED Containing the Same
According to the present invention, hole transport materials induce a substituent which turns an orientation angle to two phenylene groups of a biphenyldiamine partial structure, and an aryl group to two nitrogen atoms of the biphenyldiamine partial structure, thereby improving light emitting properties such as low driving voltage and high light emitting efficiency, and increasing thermal stability by raising rotational energy barrier of molecules and lifespan of a diode. The hole transport material is a biphenyldiamine derivative represented by chemical formula 1. Accordingly, the present invention can manufacture an organic light emitting diode (OLED) of high efficiency, low voltage, high brightness, and long lifespan by using the same.COPYRIGHT KIPO 2015
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Paragraph 0099-0102

(2016/12/01)

Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines
Carbon-nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C-N coupling to give multiply C-N coupled products in high yields. The novel C-N cross-coupling reaction was successfully applied to C-N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.
Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
p. 1437 - 1446
(2015/11/16)

Palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts
We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.
Green, Rebecca A.,Hartwig, John F.
supporting information
p. 4388 - 4391
(2015/01/08)

Stable nickel(0) phosphites as catalysts for C-N cross-coupling reactions
Herein we describe the design and preparation of inexpensive, air-stable nickel phosphite-based catalysts for use in the C-N cross-coupling reaction. The combination of nickel tetrakis(triphenyl phosphite) {Ni[P(OPh) 3]4} and 1,1'-bis(diphenylphosphino)ferrocene (dppf), and in particular a newly developed catalyst (dppf)Ni[P(OPh)3] 2, were found to be extremely effective in catalyzing a range of amination reactions of anilines and amines with aryl chlorides. This new catalyst system offers an alternative to the bis(cyclooctadienyl)nickel [Ni(COD)2] and palladium(0) catalysts commonly used for C-N bond formation.
Kampmann, Sven S.,Sobolev, Alexandre N.,Koutsantonis, George A.,Stewart, Scott G.
supporting information
p. 1967 - 1973
(2014/07/07)

Synthesis of benzo-γ-sultams via the Rh-catalyzed aromatic C-H functionalization of diazosulfonamides
An efficient synthesis of 1-aryl-benzo-γ-sultams, 1-aryl-1,3-dihydrobenzo[c]isothiazole-2,2-dioxides, was achieved in 65-99% yields via the Rh-catalyzed intramolecular aromatic C-H functionalization of N,N-diaryl diazosulfonamides with 0.5 mol% Rh2(oct)4 as the catalyst. This journal is the Partner Organisations 2014.
Yang, Zhanhui,Xu, Jiaxi
supporting information
p. 3616 - 3618
(2014/04/03)