- Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes
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A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.
- Li, Meina,Kong, Duanyang,Zi, Guofu,Hou, Guohua
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p. 680 - 687
(2017/04/26)
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- Detrifluoroacetylation of 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones as a convenient synthetic strategy for acyl cyanides Dedicated to Academician Valery N. Charushin on his 65th birthday.
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A reaction reinvestigation of fluorinated 1,3-dicarbonyl compounds with NaNO2 in acidic conditions revealed the formation of corresponding 1,1,1-trifluoro-3-hydroxyimino-butan-2,4-diones which predominantly isolated as hydrates. A novel synthesis of ethoxy-, alkyl-, (het)aryl substituted carbonylcyanides via acid-catalyzed detrifluoroacetylation of obtained 2-hydroxyimino derivatives of 1,3-dicarbonyl compounds was described.
- Bazhin, Denis N.,Kudyakova, Yulia S.,Nemytova, Natalia A.,Burgart, Yanina V.,Saloutin, Victor I.
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- Reactions of Zirconocene-1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles
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Insertion of acyl cyanides into azazirconacyclopentenes derived from 1,3-azadienes has been described, which affords acyl- or non-acyl-substituted pyrroles upon acidic quenching. These reactions are initialized through C=O insertion into the azazirconacycle to afford seven-membered oxaazazirconacycles. In the cases of 1,4- or 1,2,4-substituted azadienes, addition of a second molecule of acyl cyanide followed by cyclization upon acidic quenching leads to acyl-substituted pyrroles. In the cases of 1,3,4-substituted azadienes, the addition of a second molecule of acyl cyanide cannot proceed due to the steric hindrance caused by the R3 group on the zirconium intermediate. Acidic quenching of the resulting zirconium intermediate affords non-acyl-substituted pyrroles.
- Xiong, Meijun,Yu, Shasha,Xie, Xin,Li, Shi,Liu, Yuanhong
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supporting information
p. 5597 - 5601
(2015/12/23)
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- Conjugate hydrocyanation of aromatic enones using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
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A selective conjugate hydrocyanation of aromatic enones by a one-pot, two-step procedure using potassium hexacyanoferrate(II) as an original eco-friendly cyanide source, potassium hydroxide as a base, and benzoyl chloride as a promoter was described. This protocol has the advantages of a nontoxic cyanide source, high yield, and simple workup procedure. Georg Thieme Verlag Stuttgart · New York.
- Li, Zheng,Liu, Chenhui,Zhang, Yupeng,Li, Rongzhi,Ma, Ben,Yang, Jingya
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supporting information
p. 2567 - 2571
(2012/11/13)
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- One-Pot Three-Component Solvent-Free Cyanoaroylation of Aldehydes Using Potassium Hexacyanoferrate(II) as an Environmentally Benign Cyanide Source
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An efficient method for one-pot three-component solvent-free cyanoaroylation of aldehydes using potassium hexacyanoferrate(II) as an environmentally benign cyanide source and triethylamine as a catalyst has been described. This method has advantages of not using strongly toxic cyanating agents and volatile organic solvents. In addition, the product was obtained in high yield using a simple workup procedure.
- Li, Zheng,Tian, Guoqiang,Ma, Yuanhong
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supporting information; experimental part
p. 2164 - 2168
(2010/10/21)
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- AgI-PEG400-KI catalyzed environmentally benign synthesis of aroyl cyanides using potassium hexacyanoferrate(II) as the cyanating agent
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A practical cyanation of aroyl chlorides with 0.2 equivalent of non-toxic cyanide source, K4[Fe(CN)6], 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system is described. The reactions were performed in DMF at room temperature and provided the corresponding aroyl cyanides in 64-89% yield, typically in less than ten hours. Georg Thieme Verlag Stuttgart.
- Li, Zheng,Shi, Shengyi,Yang, Jingya
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p. 2495 - 2497
(2008/02/11)
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- A novel heterogeneous synthesis of acyl cyanides catalyzed by PEG400 and zinc iodide
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Aroyl cyanides were readily synthesized in moderate yields by the cyanation of aroyl chlorides with dry powdered potassium cyanide under the catalysis of PEG400 and zinc iodide in dichloromethane at room temperature. A preliminary study on the one-pot preparation of acetyl cyanide was also reported.
- Cao, Yu-Qing,Du, Yun-Fei,Chen, Bao-Hua,Li, Ji-Tai
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p. 2951 - 2957
(2007/10/03)
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- Flash vacuum pyrolysis of 3-oxo-2-arylhydrazonopropanals and related derivatives
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Flash vacuum pyrolysis (FVP) of 3-oxo-2-arylhydrazonopropanals at 500°C and 0.02 Torr yielded the corresponding derivatives of anilines, N-formylanilines, N-benzoylanilines and benzoylnitriles. Similar FVP of phenylhydrazonomalononitrile, phenylhydrazonoa
- Ibrahim, Yehia A,Kaul, Kamini,Al-Awadi, Nouria A
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p. 10171 - 10176
(2007/10/03)
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- Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides
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The effects of alkali metal cyanide impregnated on Amberlite XAD resins (KCN/XAD, NaCN/XAD) have been examined using the cyanation of benzoyl chloride.In benzene, benzoyl cyanide was obtained in a very high yield with high selectivity under mild conditions.It is proposed that the reaction occurs on the surface of the resin.On the basis of the result obtained in the absence of any solvent, the reactivity of KCN/XAD toward dimerization of benzoyl cyanide has been found to be much poorer than that of KCN in solution.Although the reaction of acyl chlorides with KCN/XADor NaCN/XAD in benzene gave various acyl cyanides in good to excellent yields, no aliphatic acyl cyanide could be obtained.
- Sukata, Kazuaki
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p. 1085 - 1090
(2007/10/02)
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- TRIBUTYLTIN CYANIDE: A FACILE CYANATING AGENT OF ACYL CHLORIDES
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Tributyltin cyanide was prepared from tributyltin chloride and potassium cyanide, and was found to be an efficient cyanation reagent for acyl chlorides to give acyl cyanides in excellent yields.
- Tanaka, Masato
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p. 2959 - 2962
(2007/10/02)
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- Process for the production of acyl cyanides (B)
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There are prepared acyl cyanides of the formula STR1 where R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and which also can be substituted by one or more phenyl groups or halogen atoms, preferably chlorine, or R is preferably a cycloalkyl group having 3 to 8 carbon atoms, preferably cyclopropyl, which can have one or more 1 to 3 carbon atom alkyl or halogen, preferably chlorine, substituents wherein in all of the above set forth substitutions the halogen atoms and the phenyl groups are not on the carbon atom adjacent to the carbonyl group or R is a substituted phenyl group, a naphthyl group, a substituted naphthyl group or a five membered heterocyclic group, e.g., furyl, thienyl or alkyl substituted thienyl, wherein the substituents on the phenyl or naphthyl are halogen atoms, nitro groups or alkyl or alkoxy groups having 1 to 5 carbon atoms. The process comprises reacting an acyl halide of the formula in which R is as defined above and Hal is a chlorine or bromine atom, with a mixture consisting of about 0.1 to 5 equivalents of the alkali metal cyanide and about 0.05 to 2 equivalents of the copper (I) salt at a temperature of about 50° to 180° C in the presence of a carboxylic acid nitrile inert under the reaction conditions employed. Certain of the compounds are novel per se.
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