- Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents
-
The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).
- Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro,Correa-Campillo, Jara
-
supporting information
p. 1205 - 1210
(2022/02/25)
-
- A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides
-
Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.
- Bartling, Stephan,Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Rabeah, Jabor,Rockstroh, Nils,Senthamarai, Thirusangumurugan
-
supporting information
p. 508 - 531
(2022/02/11)
-
- Synthesis of Nitrile-Functionalized Polydentate N-Heterocycles as Building Blocks for Covalent Triazine Frameworks
-
Covalent triazine frameworks (CTFs) based on polydentate ligands are highly promising supports to anchor catalytic metal complexes. The modular nature of CTFs allows to tailor the composition, structure, and function to its specific application. Access to a broad range of chelating building blocks is therefore essential. In this respect, we extended the current available set of CTF building blocks with new nitrile-functionalized N-heterocyclic ligands. This paper presents the synthesis of the six ligands which vary in the extent of the aromatic system and the denticity. The new building blocks may help in a rational design of enhanced support materials in catalysis.
- Debruyne, Maarten,Everaert, Jonas,Heugebaert, Thomas S. A.,Stevens, Christian V.,Van Der Voort, Pascal,Van Hecke, Kristof,Van Speybroeck, Veronique,Vanden Bussche, Flore
-
-
- Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)
-
The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)
- -
-
Paragraph 0080; 0081
(2020/09/12)
-
- Method for continuous preparation of nitriles in a pipelined reactor (by machine translation)
-
The method comprises the following steps that a tin catalyst is coated on the inner wall of the pipeline reactor; and the method comprises the following steps: coating a tin catalyst on the inner wall of the pipeline reactor. The amide solution and the catalytic auxiliary agent are mixed and then sent to a pipeline reactor, and the amide is dehydrated to generate nitrile at the reaction pressure of 0.1 - 2.0 mpa and 100 - 200 °C reaction temperature. The resulting reaction product was separated to give the crude product of the nitrile to which the amide corresponded. In the pipeline reactor, the corresponding nitrile is continuously prepared under the action of the tin catalyst, a dehydrating agent is not needed, byproducts only are water, and three wastes are reduced. (by machine translation)
- -
-
Paragraph 0036-0047; 0056; 0058
(2020/12/14)
-
- Zn-catalyzed cyanation of aryl iodides
-
We report the first example of zinc-catalyzed cyanation of aryl iodides with formamide as the cyanogen source. The transformation was promoted by the bisphosphine Nixantphos ligand. Under optimized conditions, a variety of electron-donating and electron-withdrawing aryl iodides were converted into nitrile products in good to excellent yields. This approach is an exceedingly simple and benign method for the synthesis of aryl nitriles and is likely to proceed via a dinuclear Zn-concerted catalysis.
- Zhao, Lulu,Dong, Yanan,Xia, Qiangqiang,Bai, Jianfei,Li, Yuehui
-
p. 6471 - 6477
(2020/06/08)
-
- Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation
-
There is a strong incentive for environmentally benign and sustainable production of organic nitriles to avoid the use of toxic cyanides. Here we report that manganese oxide nanorod-supported single-site Ru catalysts are active, selective, and stable for oxidative cyanation of various alcohols to give the corresponding nitriles with molecular oxygen and ammonia as the reactants. The very low amount of Ru (0.1 wt %) with atomic dispersion boosts the catalytic performance of manganese oxides. Experimental and theoretical results show how the Ru sites enhance the ammonia resistance of the catalyst, bolstering its performance in alcohol dehydrogenation and oxygen activation, the key steps in the oxidative cyanation. This investigation demonstrates the high efficiency of a single-site Ru catalyst for nitrile production.
- Gates, Bruce C.,Guan, Erjia,Meng, Xiangju,Wang, Chengtao,Wang, Hai,Wang, Liang,Wang, Sai,Xiao, Feng-Shou,Xu, Dongyang,Xu, Hua,Yang, Bo,Zhang, Jian
-
p. 6299 - 6308
(2020/07/21)
-
- Method for continuous preparation of nitriles by amides (by machine translation)
-
The method comprises the following steps: preparing a lead salt supported by a molecular sieve by a lead salt and a molecular sieve through an impregnation method; and filling a molecular sieve-loaded lead catalyst into a fixed bed reactor. The amide or amide solution is sent into a fixed bed reactor from the top of the fixed bed to be subjected to catalytic dehydration, and the obtained reaction product is led out from the bottom of the fixed bed. The reaction product is separated to obtain the crude product of the nitrile corresponding to the amide. A fixed bed continuous production process is adopted, the reaction process is simple, the production efficiency is high, the product post-treatment is simple, and industrial production is easy to realize. (by machine translation)
- -
-
Paragraph 0033-0054; 0061-0066
(2020/12/15)
-
- A carboxamide is the cyanogen source of aromatic nitrile to the preparation method of the (by machine translation)
-
The invention discloses a method for preparing aromatic nitrile, is under the action of the nickel catalyst, in order to carboxamide is the cyanogen source, and with various substituents haloarene coupled reactions, preparing aromatic nitrile. The reaction temperature is 100 - 160 °C, the reaction time is 6 - 24 hours. It overcomes the traditional aromatic nitrile of the synthesis method operation of complex steps, requires the use of a toxic, more expensive, functionalization of the cyanogen source as the reaction raw material and the like. Compared with the traditional method, this method is simple to use cheap, green non-toxic of the formamide is cyano sources; without the need of external dehydrating agent, formamide in the nickel catalyst of the catalytic dehydration at the same time, with a nickel catalyst in coordination with the halogenated aromatic hydrocyanation, more economic, high-efficiency, environmental protection; at the same time the method exhibits good substrate universality, to air, moisture, light are not sensitive, high yield, product separation and purification is simple, with wide application. (by machine translation)
- -
-
Paragraph 0015; 0016; 0017; 0018-0024; 0116; 0117-0122
(2019/05/08)
-
- Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions
-
The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.
- Yang, Luo,Liu, Yu-Ting,Park, Yoonsu,Park, Sung-Woo,Chang, Sukbok
-
p. 3360 - 3365
(2019/03/26)
-
- Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)2: A Route to Aryl Nitriles
-
A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C-O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.
- Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
-
supporting information
p. 2753 - 2756
(2018/05/22)
-
- Practical CuCl/DABCO/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant
-
A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCl/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature. A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.
- Hu, Yongke,Chen, Lei,Li, Bindong
-
supporting information
p. 464 - 466
(2017/11/13)
-
- Pd-Catalyzed Cyanation of (Hetero)Aryl Halides by Using Biphosphine Ligands
-
Tetraadamantylbiphosphine (TABP; L1), which showed superior activity in the palladium-catalyzed cyanation of 4-chloroanisole compared to standard phosphines, was synthesized as a new ligand. The generality of the new catalytic system was shown by the cyanation reaction of approximately 30 (hetero)aryl halides including hindered, electron-rich, and electron-poor aryl chlorides. These reactions constitute the first examples of using biphosphine ligands in Pd-catalyzed coupling reactions.
- Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
-
supporting information
p. 67 - 70
(2017/11/27)
-
- Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
-
The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
- -
-
Paragraph 0043; 0045; 0192-0194
(2018/11/03)
-
- HETEROCYCLIC COMPOUNDS
-
The present invention relates to compounds of the general formula (1) wherein the variables are defined as given in the description and claims. The invention further relates to uses of and to, processes and intermediates related to compounds of the general formula (I), wherein Q is wherein the substituents of I, Ia and Ib are as defined in description and claims.
- -
-
Page/Page column 97
(2018/07/29)
-
- Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
-
We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.
- Yu, Peng,Morandi, Bill
-
supporting information
p. 15693 - 15697
(2017/12/02)
-
- Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature
-
The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).
- Kim, Kicheol,Hong, Soon Hyeok
-
supporting information
p. 2345 - 2351
(2017/07/22)
-
- Decarbonylative Cyanation of Amides by Palladium Catalysis
-
Transition-metal-catalyzed cyanation of aryl halides is a process of significant importance in the preparation pharmaceuticals, organic materials and agrochemicals. Here, we demonstrate a palladium-catalyzed decarbonylative cyanation of amides by highly selective carbon-nitrogen bond cleavage for the synthesis of a wide range of aryl nitriles. The utility of this technology is demonstrated by the synthesis of isotopically labeled aryl nitriles and orthogonal cross-coupling reactions of bench-stable amides to establish cross-coupling synthons with opposite polarity.
- Shi, Shicheng,Szostak, Michal
-
supporting information
p. 3095 - 3098
(2017/06/23)
-
- General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
-
A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
- Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
-
supporting information
p. 2118 - 2121
(2017/04/27)
-
- Discovery and optimization of a series of imidazo[4,5-b]pyrazine derivatives as highly potent and exquisitely selective inhibitors of the mesenchymal–epithelial transition factor (c-Met) protein kinase
-
Aberrant c-Met activation has been implicated in multiple tumor oncogenic processes and drug resistance. In this study, a series of imidazo[4,5-b]pyrazine derivatives was designed and synthesized, and their inhibitory activities were evaluated in vitro. Structure–activity relationship (SAR) was investigated systematically and docking analysis was performed to elucidate the binding mode, leading to the identification of the most promising compound 1D-2 which exhibited significant inhibitory effect on both enzymatic (IC50?=?1.45?nM) and cellular (IC50?=?24.7?nM in H1993 cell line) assays, as well as exquisite selectivity and satisfactory metabolic stability in human and rat liver microsomes.
- Zhao, Fei,Zhang, Jing,Zhang, Leduo,Hao, Yu,Shi, Chen,Xia, Guangxin,Yu, Jianxin,Liu, Yanjun
-
supporting information
p. 4281 - 4290
(2016/08/23)
-
- Quinoline compounds and preparation method thereof, and intermediate, pharmaceutical composition and application of quinoline compounds
-
The invention discloses quinoline compounds and a preparation method thereof, and an intermediate, a pharmaceutical composition and application of quinoline compounds. The invention provides quinoline compounds disclosed as Formula 1, and pharmaceutically acceptable salts, solvates, metabolites, metabolism precursors or pharmaceutical precursors thereof. The quinoline compounds have favorable inhibitory effects on tyrosine kinase C-Met, and can be used for preparing drugs for prevention, treatment or auxiliary treatment on multiple diseases related to C-Met expression or activity, and especially neoplastic diseases.
- -
-
Paragraph 0434-0436
(2018/02/04)
-
- Cyanation of Phenol Derivatives with Aminoacetonitriles by Nickel Catalysis
-
Generation of useful arylnitrile structures from simple aromatic feedstock chemicals represents a fundamentally important reaction in chemical synthesis. The first nickel-catalyzed cyanation of phenol derivatives with metal-free cyanating agents, aminoacetonitriles, is described. A nickel-based catalytic system consisting of a unique diphosphine ligand such as dcype or dcypt enables the cyanation of versatile phenol derivatives such as aryl carbamates and aryl pivalates. The use of aminoacetonitriles as a cyanating agent leads to an environmentally and easy-to-use method for arylnitrile synthesis.
- Takise, Ryosuke,Itami, Kenichiro,Yamaguchi, Junichiro
-
supporting information
p. 4428 - 4431
(2016/10/12)
-
- Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage
-
Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).
- Dutta, Uttam,Lupton, David W.,Maiti, Debabrata
-
supporting information
p. 860 - 863
(2016/03/01)
-
- HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
-
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
- Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
-
p. 40950 - 40952
(2015/05/20)
-
- NOVEL 3,5-DISUBSTITUTED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUTED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN, ETC
-
The present invention provides compounds useful as c-Met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of c-Met kinase mediated disease or disorders with them.
- -
-
-
- A new oxazole ligand for the copper-catalyzed cyanation of aryl halides with K4 [Fe(CN)6]
-
An efficient and new method for the copper-catalyzed cyanation of aryl halides is reported using a new oxazole ligand and K4Fe(CN) 6 as a non-toxic source of cyanide.
- Sajadi, S. Mohammad,Maham, Mehdi
-
p. 136 - 140
(2014/03/21)
-
- Copper iodide nanoparticles-catalysed cyanation of aryl halides using non-toxic K4[Fe(CN)6] in the presence of 1,2-bis(5-tetrazolyl)benzene as an efficient ligand
-
Cyanation of aryl bromides were carried out with K4[Fe(CN) 6] in the presence of catalytic amounts of a copper salt and 1,2-bis(5-tetrazolyl)benzene as a ligand under thermal conditions. This method has the advantages of high yields, simple methodology and easy work up.
- Maham, Mehdi,Bahari, Siavash
-
p. 291 - 294
(2014/06/09)
-
- Efficient copper-catalyzed cyanation of aryl bromides using 1,3-phenylene-bis-(1h)-tetrazole as an efficient ligand
-
A new method for the synthesis of aryl nitriles has been developed by the cyanation of aryl bromides with K4Fe(CN)6 as a cyanide source in the presence of Cu(OAc)2.H2O as an inexpensive catalyst and a 1,3-phenylene-bis-(1H)-tetrazole ligand. This method has the advantages of high yield, simple methodology and easy work-up.
- Bahari, Siavash,Rezaei, Akbar
-
p. 519 - 523
(2014/05/20)
-
- Cyanation of unactivated aryl chlorides and aryl mesylates catalyzed by palladium and hemilabile MOP-type ligands
-
Palladium-catalyzed cyanation of aryl halides and pseudo halides with potassium hexacyanoferrate is described employing the hemilabile, bulky, and electron-rich MOP-type ligands. When the mixture of t-BuOH and H2O was used as the solvent and K2CO3 as the base, the MOP-type ligands showed high efficiency for the palladium-catalyzed cyanation. The effect of ligand structure was studied in detail, and 2-di-tert-butylphosphino-2′-isopropoxy-1,1′-binaphthyl was the more effective for the cyanation. The catalyst system allows the cyanation of unactivated aryl chlorides, and even aryl mesylates to occur in good yields. Furthermore, the reactivity of different arylated reagents in the catalytic system was found to be: ArBr > ArCl >> ArOMs > ArOSO2Im > ArOSO2NMe2.
- Tu, Yahui,Zhang, Yi,Xu, Sheng,Zhang, Zhaoguo,Xie, Xiaomin
-
supporting information
p. 2938 - 2942
(2015/01/16)
-
- The Pd(0) nanoparticles stabilized by collagen fibers as a recyclable heterogeneous catalyst for the cyanation of aryl bromides using k4fe(cn)6 as non-toxic source of cyanide
-
A new method for the synthesis of aryl nitriles has been developed by the cyanation of aryl bromides in the presence of the Pd(0) nanoparticles stabilized by collagen fibers as a highly active, air-stable and recyclable heterogeneous catalyst. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst was recovered and reused several times without the significant loss of its catalytic performance.
- Bahari, Siavash
-
p. 523 - 526
(2013/08/23)
-
- NOVEL 3,5-DISUBSTITUED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN KINASES
-
The present invention provides compounds useful as C-met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of C-met kinase mediated diseases or disorders with them.
- -
-
-
- METALLOENZYME INHIBITOR COMPOUNDS
-
The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
- -
-
Page/Page column 25
(2013/02/28)
-
- The synthesis of N-heterocycles via copper/TEMPO catalysed aerobic oxidation of amino alcohols
-
N-Heterocycles can be prepared using alcohol oxidation as a key synthetic step. Herein we report studies exploring the potential of Cu/TEMPO as an aerobic oxidation catalyst for the synthesis of substituted indoles and quinolines.
- Flanagan, James C. A.,Dornan, Laura M.,McLaughlin, Mark G.,McCreanor, Niall G.,Cook, Matthew J.,Muldoon, Mark J.
-
supporting information; experimental part
p. 1281 - 1283
(2012/06/04)
-
- An expedient Pd/DBU mediated cyanation of aryl/heteroaryl bromides with K4[Fe(CN)6]
-
A practical Pd(PPh3)4/DBU catalytic system for the synthesis of pharmaceutically relevant aminopyridine nitrile intermediates, as well as a variety of other aryl nitriles using non-toxic K4[Fe(CN) 6] has been developed. The key features of our new protocol for cyanation lie in that the reaction can be carried out with readily available Pd(PPh3)4 under mild and green conditions, even without the assistance of other ligands. The Royal Society of Chemistry 2012.
- Zhang, Dengyou,Sun, Haifeng,Zhang, Lei,Zhou, Yu,Li, Chunpu,Jiang, Hualiang,Chen, Kaixian,Liu, Hong
-
supporting information; experimental part
p. 2909 - 2911
(2012/03/27)
-
- CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
-
Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.
- -
-
Page/Page column 21
(2012/10/08)
-
- Efficient cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by a palladium-indolylphosphine complex
-
This study describes a general palladium-catalyzed cyanation of aryl bromides using K4[Fe(CN)6] as the cyanide surrogate. The reactions can be successfully conducted under mild reaction conditions (at 50 °C) in mixed solvents (water/MeCN = 1:1) without any surfactant additives, and afford the desired aryl nitriles in good-to-excellent yields. Particularly noteworthy is that this system allows the mildest reaction temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K 4[Fe(CN)6] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing -PCy 2 moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding ligands with -PPh2 group.
- Yeung, Pui Yee,Tsang, Chun Pui,Kwong, Fuk Yee
-
experimental part
p. 7038 - 7041
(2012/01/05)
-
- NOVEL 3,5-DISUBSTITUTED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUTED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF PROTEIN KINASES
-
The present invention provides, inter alia, compounds of formula I as protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
- -
-
-
- NOVEL 3,5-DISUBSTITUED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF PROTEIN KINASES
-
The present invention provides, inter alia, compounds of formula ΙΑ,ΙΙΑ and III as protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
- -
-
-
- CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
-
Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.
- -
-
Page/Page column 36
(2011/07/30)
-
- A mild and efficient palladium-catalyzed cyanation of aryl chlorides with K4[Fe(CN)6]
-
An efficient palladium-catalyzed cyanation of aryl chlorides is established. In the presence of a highly effective Pd/CM-phos catalyst, cyanation of aryl chlorides proceeds at 70 °C in general, which is the mildest reaction temperature achieved so far for this process. Common functional groups such as keto, aldehyde, ester, nitrile and-NH2, and heterocyclic coupling partners including N-H indoles are well tolerated. Moreover, a sterically hindered nonactivated ortho,ortho-disubstituted electrophile is shown to be a feasible coupling partner in cyanation.
- Yeung, Pui Yee,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
-
supporting information; experimental part
p. 648 - 651
(2011/04/15)
-
- A mild and efficient palladium-catalyzed cyanation of aryl mesylates in water or tBuOH/water
-
Cool and compatible: Aryl mesylates and tosylates underwent palladium-catalyzed cyanation under mild, aqueous conditions at 65-80°C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl, Ts=p-toluenesulfonyl.
- Yeung, Pui Yee,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
-
supporting information; experimental part
p. 8918 - 8922
(2011/02/24)
-
- Application of polymer-supported triphenylphosphine and microwave irradiation to the palladium-catalyzed cyanation of aryl triflates
-
A variety of aryl nitriles were prepared in excellent yield from the palladium(II) acetate-catalyzed cross-coupling of aryl triflates and zinc cyanide under microwave irradiation conditions. To facilitate purification, polymer-supported triphenylphosphine was used as the palladium ligand. Comparison to the corresponding thermal conditions revealed much shorter reaction times with comparable yields. Copyright Taylor & Francis Group, LLC.
- Srivastava, Rajiv R.,Zych, Andrew J.,Jenkins, David M.,Wang, Hong-Jun,Chen, Zhen-Jia,Fairfax, David J.
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p. 431 - 438
(2007/10/03)
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- An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid
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Aryl and arylvinyl nitriles have been prepared in good yields from the corresponding bromides with potassium hexacyanoferrate (II) using palladium-catalyzed reactions in ionic liquid under microwave irradiation. Georg Thieme Verlag Stuttgart.
- Li, Lian-Hua,Pan, Zhen-Liang,Duan, Xin-Hua,Liang, Yong-Min
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p. 2094 - 2098
(2008/02/05)
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