- One-pot synthesis of aldoximes from alkenes: Via Rh-catalysed hydroformylation in an aqueous solvent system
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Aldoxime synthesis directly starting from alkenes was successfully achieved through the combination of hydroformylation and subsequent condensation of the aldehyde intermediate with aqueous hydroxylamine in a one-pot process. The metal complex Rh(acac)(CO)2 and the water-soluble ligand sulfoxantphos were used as the catalyst system, providing high regioselectivities in the initial hydroformylation. A mixture of water and 1-butanol was used as an environmentally benign solvent system, ensuring sufficient contact of the aqueous catalyst phase and the organic substrate phase. The reaction conditions were systematically optimised by Design of Experiments (DoE) using 1-octene as a model substrate. A yield of 85% of the desired linear, terminal aldoxime ((E/Z)-nonanal oxime) at 95% regioselectivity was achieved. Other terminal alkenes were also converted successfully under the optimised conditions to the corresponding linear aldoximes, including renewable substrates. Differences of the reaction rate have been investigated by recording the gas consumption, whereby turnover frequencies (TOFs) >2000 h-1 were observed for 4-vinylcyclohexene and styrene, respectively. The high potential of aldoximes as platform intermediates was shown by their subsequent transformation into the corresponding linear nitriles using aldoxime dehydratases as biocatalysts. The overall reaction sequence thus allows for a straightforward synthesis of linear nitriles from alkenes with water being the only by-product, which formally represents an anti-Markovnikov hydrocyanation of readily available 1-alkenes.
- Gr?ger, H.,Guntermann, A.,Hinzmann, A.,Jolmes, T.,Panke, D.,Plass, C.,R?sler, J.,Seidensticker, T.,Terhorst, M.,Vogt, D.,Vorholt, A. J.
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p. 7974 - 7982
(2020/11/30)
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- Preparation method of alkyl nitrile compound
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The invention discloses a preparation method of an alkyl nitrile compound. Specifically, the preparation method comprises the following step: in an organic solvent, in the presence of a protective gasand under the action of a catalyst, carrying out a reduction reaction as shown in the specification on olefin as shown in a formula I, a cyanation reagent and water, wherein the alkyl nitrile compound 1 is a compound II and/or a compound III. The preparation method provided by the invention is mild in condition, can realize hydrocyanation of olefin more safely and efficiently, and has good substrate universality and functional group compatibility.
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Paragraph 0214-0216
(2020/08/18)
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- Tuning of active sites in M/TiO2 for photocatalytic cyanation of olefins with high regioselectivity
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The detailed structure of active sites plays an important role for the determination of catalytic performance. Herein, catalytic active sites of M/TiO2 for photocatalytic cyanation of olefins are tuned by delicate manipulation of the metal kinds, metal loading amount and pretreatment processes. It was found that the 0.1% Pt/P25 catalyst reduced at 300 °C possessed high metal dispersion and suitable oxygen defects on TiO2, and thus exhibited the best catalytic performance with high specific speed of time yield and high selectivity. A wide scope of olefin substrates could be converted to the corresponding nitriles with high atom efficiency and anti-Markovnikov regioselectivity under mild conditions for the optimized Pt/P25 catalyst. The reaction mechanism based on radical coupling of acetonitrile and olefins was also discussed. This approach offers an environmental-friendly platform for the selective activation of C-H bonds of acetonitrile and will bring potential applications for hydrofunctionalization of olefins.
- Bao, Jingxian,Huang, Min,Sun, Yuhan,Wu, Bo,Zhang, Shuyi,Zhong, Liangshu
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- Method for preparing nitrile
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The invention provides a method for preparing nitrile. Aldoxime carboxylic ester is used as a reactant to prepare a nitrile compound. The aldoxime carboxylic ester can be completely converted into corresponding nitrile under common catalysis of ferric salt and phenol within a few minutes. The method for preparing the nitrile has the advantages of gentle reaction conditions, simple and easy-to-getused reagents, cheap and environment-friendly catalyst, wide substrate application range, simple operation, rapid reaction and the like.
- -
-
Paragraph 0015
(2019/06/13)
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- Thiocyanate radical mediated dehydration of aldoximes with visible light and air
-
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
- Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
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supporting information
p. 9701 - 9704
(2019/08/15)
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- Hydrofunctionalization of Olefins to Higher Aliphatic Alcohols via Visible-Light Photocatalytic Coupling
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Abstract: An atomically economical green protocol for the hydrofunctionalization of olefins to higher aliphatic alcohols with 100% anti-Markovnikov regioselectivity was developed via visible-light photocatalytic coupling. This method employs cheap, readily available and abundant methanol as both the C1 feedstock and the hydrogen source under visible light irradiation over CdS photocatalyst. A wide scope of olefin substrates could be hydrofunctionalized successfully to the corresponding higher alcohols with high selectivity. Besides alcohol, acetone and acetonitrile can also couple with olefins to generate the corresponding hydrofunctionalization products, suggesting promising potential industrial application. Graphical Abstract: [Figure not available: see fulltext.] Hydrofunctionalization of olefins to value-added chemicals with high selectivity was achieved via visible-light photocatalytic cross-coupling.
- Bao, Jingxian,Fan, Yonghui,Zhang, Shuyi,Zhong, Liangshu,Wu, Minghong,Sun, Yuhan
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-
- Method for Selective Oxidation of Amines Using Two Dimensional Heterogeneous Nano-catalysts with Ruthenium Dispersed on Exfoliated Sheets of Molybdenum Disulfide
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Disclosed is a method for selectively oxidizing an amine-based compound to convert the same into compounds such as nitrile using a two-dimensional heterogeneous nanocatalyst containing ruthenium supported, at high dispersion rate, on an exfoliated layer of molybdenum disulfide which is a layered transition metal dichalcogenide (LTMD).COPYRIGHT KIPO 2019
- -
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Paragraph 0144-0147
(2019/03/13)
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- Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile
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Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.
- Bhunia, Anup,Bergander, Klaus,Studer, Armido
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supporting information
p. 16353 - 16359
(2018/11/25)
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- Hydrofunctionalization of olefins to value-added chemicals: Via photocatalytic coupling
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A green strategy was developed for the synthesis of various value-added chemicals using methanol, acetonitrile, acetic acid, acetone and ethyl acetate as the hydrogen source by coupling them with olefins over heterogeneous photocatalysts. A radical coupling mechanism was proposed for the hydrofunctionalization of olefins with methanol to higher aliphatic alcohols over the Pt/TiO2 catalyst as the model reaction. C-H bond cleavage and C-C bond formation between photogenerated radicals and terminal olefins were accomplished in a single reaction at high efficiency. Our approach is atomically economical with high anti-Markovnikov regioselectivity and promising application potential under mild reaction conditions.
- Fan, Yonghui,Li, Shenggang,Bao, Jingxian,Shi, Lei,Yang, Yanzhang,Yu, Fei,Gao, Peng,Wang, Hui,Zhong, Liangshu,Sun, Yuhan
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supporting information
p. 3450 - 3456
(2018/08/06)
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- Amino acid derived ionic liquid supported iron Schiff base catalyzed greener approach for the aerobic oxidation of amines to nitriles
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Amino acid dl-threonine derived ionic liquid was treated with salicylaldehyde to give corresponding Schiff base which subsequently is complexed with iron and used as a green catalyst for aerobic oxidation of amines under solvent-less conditions. The developed catalyst was readily synthesized, reusable, and exhibited superior catalytic activity owing to the synergistic effect of ionic liquid moiety. The developed catalyst was found to be quite stable and could be reused for several runs without any significant loss in catalytic activity.
- Varyani, Manish,Khatri, Praveen K.,Jain, Suman L.
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p. 723 - 727
(2016/02/09)
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- METHOD FOR THE CONTROLLED HYDROFORMYLATION AND ISOMERIZATION OF A NITRILE/ESTER/OMEGA UNSATURATED FATTY ACID
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A method to synthesize a fatty nitrile/ester aldehyde comprising the following steps: 1) hydroformylation of a ω-unsaturated fatty nitrile/ester/acid substrate under particular conditions of partial pressure, temperature, reaction time, conversion rate of the ω-unsaturated fatty nitrile/ester/acid reactant, catalyst, [substrate]/[metal] molar ratio and [ligand]/[metal] molar ratio so as after the reaction to obtain: a hydroformylation product comprising at least one fatty nitrile/ester/acid aldehyde of formula: OHC—(CH2)r+2—R, andan isomerate comprising at least one fatty nitrile/ester/acid isomer with internal unsaturation in which at least 80% of the internal isomer(s) of the isomerate are formed of the ω-1 unsaturated isomer of formula CH3—CH═CH—(CH2)r?1—R; followed by:2) separation and recovery of the fatty nitrile/ester/acid aldehyde and of the isomerate.
- -
-
Paragraph 0166
(2016/05/24)
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- Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp3)-C(sp2) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes
-
A transition-metal-free deacylative C(sp3)-C(sp2) bond cleavage for the synthetically practical oxidative amination of ketones and aldehydes to nitriles is first described, using cheap and commercially abundant NaNO2 as the oxidant and the nitrogen source. Various nitriles bearing aryl, heteroaryl, alkyl, and alkenyl groups could be smoothly obtained from ketones and aldehydes in high yields, avoiding highly toxic cyanides or transition metals.
- Ge, Jing-Jie,Yao, Chuan-Zhi,Wang, Mei-Mei,Zheng, Hong-Xing,Kang, Yan-Biao,Li, Yadong
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supporting information
p. 228 - 231
(2016/02/03)
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- A Mild TEMPO-Catalyzed Aerobic Oxidative Conversion of Aldehydes into Nitriles
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An efficient method to prepare nitriles from aldehydes using hexamethyldisilazane (HMDS) as the nitrogen source has been developed. The reactions were performed with 2,2,6,6-tetramethylpiperidine l-oxyl (TEMPO) as the catalyst, NaNO2 or TBN as the co-catalyst, and molecular oxygen as the terminal oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles in good to excellent yields.
- Fang, Chaojie,Li, Meichao,Hu, Xinquan,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Jin, Liqun,Shen, Zhenlu
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p. 1157 - 1163
(2016/04/19)
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- Electrochemical synthesis of nitriles from aldehydes using TEMPO as a mediator
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A novel electrochemical route to generate nitriles from aldehydes under mild conditions using a catalytic amount of TEMPO (2,2,6,6-tetramethylpiperidinyl-l-oxy) as the mediator and hexamethyldisilazane as the nitrogen source in the presence of acetic acid has been developed. A variety of aromatic, heteroaromatic and aliphatic aldehydes have been converted to their corresponding nitriles in good to excellent yields. A plausible reaction mechanism is proposed based on the cyclic voltammetry, in situ FTIR and the identification of intermediates.
- Chen, Qiguo,Fang, Chaojie,Shen, Zhenlu,Li, Meichao
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-
- Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3
-
The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction system is applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively. The catalytic cycle involves the formation of a vinylidenerhodium complex as a key intermediate.
- Fukumoto, Yoshiya,Tamura, Yuto,Iyori, Yasuaki,Chatani, Naoto
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p. 3161 - 3167
(2016/05/19)
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- Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis
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A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.
- Dai, Jian-Jun,Zhang, Wen-Man,Shu, Yong-Jin,Sun, Yu-Yang,Xu, Jun,Feng, Yi-Si,Xu, Hua-Jian
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p. 6793 - 6796
(2016/06/01)
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- Versatile and chemoselective transformation of aliphatic and aromatic secondary amides to nitriles
-
Triflic anhydride in combination with 2-fluoropyridine effectively dehydrates secondary amides to afford nitriles under mild reaction conditions. The reaction is general in scope and compatible with the use of aliphatic, α,β-unsaturated, aromatic, and heteroaromatic amides bearing either secondary, tertiary, or benzylic N-alkyl groups. The reaction also shows good to excellent chemoselectivity for the secondary amide and tolerates several labile functional groups.
- Geng, Hui,Huang, Pei-Qiang
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p. 3795 - 3801
(2015/06/02)
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- Rhodium versus iridium catalysts in the controlled tandem hydroformylation-isomerization of functionalized unsaturated fatty substrates
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The hydroformylation of 10-undecenitrile (1) and related unsaturated fatty substrates (H2C=CH(CH2)7CH2R; R=CO2Me, CH2Br, CHO) has been studied with rhodium, iridium, ruthenium, and palladium biphephos catalysts. The reactions proceeded effectively with all four systems, with high selectivities for the linear aldehyde (ratio of linear/branched aldehydes=99:1). The biphephos-bis[chloro(cyclooctadiene)iridium] system showed a non-optimized hydroformylation turnover frequency (TOFHF) of 770h-1 that was only approximately 5times lower than that of the rhodium-based system (TOFHF=3320h-1); the palladium and ruthenium biphephos systems were less active (TOFHF=210 and 310h-1, respectively). Upon recycling, remarkable productivities were achieved in both cases (TON≈58-000mol(1/1-int)-mol(Ir)-1 and 250-000mol(1/1-int)-mol(Rh)-1, in which int=internal olefin). Competitive isomerization of terminal to internal olefins occurred with these catalysts. Iridium biphephos systems allowed slightly better control of the distribution of the internal isomers than the rhodium biphephos catalyst, with higher ratios of 9-/8-undecenitrile (1-int). Place your bets now: Iridium-biphephos catalysts are highly effective in the controlled tandem isomerization-hydroformylation of 10-undecenitrile and related functionalized unsaturated fatty substrates.
- Ternel, Jrmy,Couturier, Jean-Luc,Dubois, Jean-Luc,Carpentier, Jean-Franois
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p. 513 - 520
(2015/03/04)
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- Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes
-
Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.
- Kawamoto, Takuji,Uehara, Shohei,Hirao, Hidefumi,Fukuyama, Takahide,Matsubara, Hiroshi,Ryu, Ilhyong
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p. 3999 - 4007
(2014/05/20)
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- Rhodium-catalyzed tandem isomerization/hydroformylation of the bio-sourced 10-undecenenitrile: Selective and productive catalysts for production of polyamide-12 precursor
-
The hydroformylation of 10-undecenenitrile (1) - a substrate readily prepared from renewable castor oil - in the presence of rhodium-phosphane catalysts systems is reported. The corresponding linear aldehyde (2) can be prepared in high yields and regioselectivities with a (dicarbonyl)rhodium acetoacetonate-biphephos [Rh(acac)(CO)2-biphephos] catalyst. The hydroformylation process is accompanied by isomerization of 1 into internal isomers of undecenenitrile (1-int); yet, it is shown that the Rh-biphephos catalyst effectively isomerizes back 1-int into 1, eventually allowing high conversions of 1/1-int into 2. Recycling of the catalyst by vacuum distillation under a controlled atmosphere was demonstrated over 4-5 runs, leading to high productivities up to 230,000 mol (2)×mol (Rh)-1 and 5,750 mol (2)×mol (biphephos)-1. Attempted recycling of the catalyst using a thermomorphic multicomponent solvent (TMS) phase-separation procedure proved ineffective because the final product 2 and the Rh-biphephos catalyst were always found in the same polar phase. Auto-oxidation of the linear aldehyde 2 into the fatty 10-cyano-2-methyldecanoic acid (5) proceeds readily upon exposure to air at room temperature, opening a new effective entry toward polyamide-12. Copyright
- Ternel, Jeremy,Couturier, Jean-Luc,Dubois, Jean-Luc,Carpentier, Jean-Francois
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p. 3191 - 3204
(2013/12/04)
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- Tert-Butylnitrite as a convenient and easy-removable oxidant for the conversion of benzylic alcohols to ketones and aldehydes
-
The oxidation of primary and secondary benzylic alcohols was achieved by using tert-butyl nitrite (t-BuONO) as a stoichiometric oxidant. Various substrates were effectively converted into the corresponding ketones or aldehydes in good to excellent yields. The reaction presumably proceeded by a nitrosyl exchange and a subsequent thermal decomposition of benzylic nitrites. This process would realize an oxidation of alcohols with oxygen in theory by combining with a reproduction of alkyl nitrites from NO and alcohols under an O2 atmosphere. In addition, almost pure oxidized products were readily obtained by simple evaporation of the reaction mixtures since t-BuONO produced only volatile side products.
- Hamasaki, Akiyuki,Kuwada, Hideyuki,Tokunaga, Makoto
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supporting information; experimental part
p. 811 - 814
(2012/03/10)
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- A non-metal catalysed oxidation of primary azides to nitriles at ambient temperature
-
A novel non-metal catalyzed oxidation of organic azides to nitriles under solvent-free conditions is presented employing catalytic amounts of KI, and DABCO in aq. TBHP at room temperature. This non-metal catalyzed oxidation of azides provides good selectivity as double and triple bonds were not oxidized under the present reaction conditions. The Royal Society of Chemistry 2012.
- Lamani, Manjunath,Devadig, Pradeep,Prabhu, Kandikere Ramaiah
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p. 2753 - 2759
(2012/11/07)
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- Iron-catalyzed alkyl-alkyl Suzuki-Miyaura coupling
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Chemoselective Suzuki-Miyaura coupling of primary and secondary alkyl halides is realized by using an iron/Xantphos catalyst. Primary and secondary alkyl bromides undergo the reaction to give the coupling products in good yields. Application to the synthe
- Hatakeyama, Takuji,Hashimoto, Toru,Kathriarachchi, Kalum K. A. D. S.,Zenmyo, Takeshi,Seike, Hirofumi,Nakamura, Masaharu
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supporting information; experimental part
p. 8834 - 8837
(2012/10/08)
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- An efficient oxidation of primary azides catalyzed by copper iodide: A convenient method for the synthesis of nitriles
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A wide range of primary azides have been efficiently oxidized by a catalytic amount of CuI and TBHP into their corresponding nitriles in aqueous solution. A variety of oxidizable functional groups were well tolerated under the reaction conditions, and oxidation of secondary azides furnished their corresponding ketones (see scheme; TBHP=tert-butyl hydroperoxide).
- Lamani, Manjunath,Prabhu, Kandikere Ramaiah
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supporting information; experimental part
p. 6622 - 6625
(2010/11/04)
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- Tin-free giese reaction and the related radical carbonylation using Alkyl iodides and cyanoborohydrides
-
Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine and carbon-chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
- Ryu, Ilhyong,Uehara, Shohei,Hirao, Hidefumi,Fukuyama, Takahide
-
supporting information; experimental part
p. 1005 - 1008
(2009/04/07)
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- Perrhenic acid-catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and α-substituted ketoximes to nitrile compounds
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The dehydration reaction of primary amides is one of the most fundamental methods for the synthesis of nitriles, and the development of environmentally benign catalytic reaction processes is needed. We surveyed a variety of metal catalysts and found that perrhenic acid was extremely effective for the dehydration of not only primary amides but also aldoximes. Typically, 1 mol % of perrhenic acid gave the corresponding nitriles from amides or aldoximes under azeotropic reflux conditions with the removal of water in toluene or mesitylene. In addition, perrhenic acid is an extremely efficient catalyst for the Beckmann fragmentation of α-substituted ketoximes to functionalized nitriles. This new catalytic system can be applied to the gram-scale synthesis of nitriles without further modifications.
- Furuya, Yoshiro,Ishihara, Kazuaki,Yamamoto, Hisashi
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p. 400 - 406
(2008/02/11)
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- Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles
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An economical and environmentally benign process for the preparation of nitriles by the dehydration of primary amides and aldoximes is catalyzed by rhenium(VII) oxo complexes such as perrhenic acid and trimethylsilylperrhenate (see scheme). The reaction proceeds at azeotropic reflux (with the removal of water) under essentially neutral conditions.
- Ishihara, Kazuaki,Furuya, Yoshiro,Yamamoto, Hisashi
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p. 2983 - 2986
(2007/10/03)
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- A clean conversion of aldehydes to nitriles using a solid-supported hydrazine
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A polymer-supported hydrazine reagent has been applied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for combinatorial chemistry programmes.
- Baxendale, Ian R.,Ley, Steven V.,Sneddon, Helen F.
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p. 775 - 777
(2007/10/03)
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- Main products and kinetics of the thermal degradation of polyamides
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The thermal degradation of the polyamides (PA) 6, 12, 66 and 612 was investigated by means of thermal analysis/ mass spectrometry (TA-MS) and pyrolysis in a german standard oven. Sample masses were about 20 and 40 mg. The heating rates used in the dynamic studies were 1, 5 and 10 K min-1. Both air and nitrogen atmospheres were utilized. The kinetic parameters were calculated from the TA-MS measurements and the main decomposition products were registered online. The evolved products from the pyrolysis oven were captured and analyzed off-line by GC/ MS.
- Herrera,Matuschek,Kettrup
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p. 601 - 607
(2007/10/03)
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- A new efficient method for the conversion of aldehydes into nitriles using ammonia and hydrogen peroxide
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Aldehydes were converted into the corresponding nitriles by a homogeneous reaction with ammonia and aqueous hydrogen peroxide in the presence of copper salts or complexes under mild conditions. (C) 2000 Elsevier Science Ltd.
- Erman,Snow,Williams
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p. 6749 - 6752
(2007/10/03)
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- MTO catalyzed oxidation of aldehyde N,N-dimethylhydrazones with hydrogen peroxide: High yield formation of nitriles and N-methylene-N-methyl N-oxide
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N,N-Dimethylhydrazones of aldehydes react with hydrogen peroxide at -50 °C in the presence of catalytic amounts of methyltrioxorhenium (MTO) to give in high yield the corresponding nitriles and N-methylene-N-methyl N-oxide.
- Rudler, Henri,Denise, Bernard
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p. 2145 - 2146
(2007/10/03)
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- Application of chelating diphosphine ligands in the nickel-catalysed hydrocyanation of alk-1-enes and ω-unsaturated fatty acid esters
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The hydrocyanation of alk-1-enes and ω-unsaturated fatty acid esters using zerovalent nickel complexes yields the corresponding nitriles and cyanoesters, which can be useful starting materials in organic synthesis.
- Goertz, Wolfgang,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.,Vogt, Dieter
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p. 1521 - 1522
(2007/10/03)
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- The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride
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Sodium hydrogen telluride reacts chemoselectively with α,β- unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to corresponding saturated nitriles with good yields.
- Blay, Gonzalo,Cardona, Luz,Garcia, Begona,Lahoz, Luisa,Pedro, Jose R.
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p. 8611 - 8618
(2007/10/03)
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- The Use of Silica Gel-Supported Ionenes as Reagents and Catalysts for Several Substitution Reactions in Toluene
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Several ionene bromides were used as reagents for the displacement of decyl methanesulfonate into 1-bromodecane.They were reactive when adsorbed by silica gel.The enhanced activities of the ionenes were hardly dependent on their structures and molecular weights but decreased gradually with increasing the amount of ionene adsorbed by silica gel.Ionene chlorides exhibited a similar enhancement of reactivity when adsorbed by silica gel.However, unlike the ionenes, a large increase in activity due to adsorption was not observed with pendant-type polycations such as poly(4-vinylpyridinium bromide) and poly.The silica gel-supported ionenes also exhibited excellent catalytic activities for solid-liquid-solid triphase substitution reactions, particularly for the reactions between 1-bromodecane and such inorganic salts as consisted of relatively hard-basic nucleophilic anions.
- Ohtani, Noritaka,Chida, Kosaku,Serita, Hajime,Matsunaga, Toshiaki,Kimura, Chikai
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p. 4371 - 4378
(2007/10/02)
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- THE REACTION OF LiAlH4/HMPA WITH OXIMES: MECHANISM AND SYNTHETIC APPLICATIONS
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Three aspects of the reaction of LiAlH4 in HMPA with oximes have been studied: the mechanism of the conversion of ketoximes into ketones, application of this reaction to the selective reduction of enones to ketones via the ene-oxime, and the conversion of aldoximes to either nitriles or aldehydes as a function of substrate structure.
- Balachander, Natarajan,Wang, Shin-Shin,Sukenik, Chaim N.
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p. 4849 - 4852
(2007/10/02)
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- Novel Functional Group Transformations involving Alkyl Phenyl Selenones
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Alkyl phenyl selenones readily undergo substitution reactions, and are valuable precursors of epoxides on reaction with aldehydes inthe presence of bases.
- Krief, Alain,Dumont, Willy,Denis, Jean-Noel
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p. 571 - 572
(2007/10/02)
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- Phosphorus Tri-iodide (PI3), a Powerful Deoxygenating Agent
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On reaction with PI3 sulphoxides, selenoxides, aldehyde oximes, and primary nitroalkanes are transformed to sulphides, selenides, and nitriles, respectively.
- Denis, Jean Noel,Krief, Alain
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p. 544 - 545
(2007/10/02)
-