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Three‐Component Synthesis of α‐Amino‐α‐aryl Carbonitriles from Arynes, Aroyl Cyanides, and N , N ‐Dimethylformamide
Author(s) -
Zhou Chao,
Wang Jing,
Jin Jisong,
Lu Ping,
Wang Yanguang
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400040
Subject(s) - chemistry , aryne , aryl , strecker amino acid synthesis , cyanide , organic chemistry , component (thermodynamics) , solvent , atom economy , medicinal chemistry , catalysis , alkyl , physics , thermodynamics , enantioselective synthesis
A general and efficient synthesis of α‐amino‐α‐aryl carbonitriles through the three‐component reaction of arynes, aroyl cyanides, and DMF in a single step is described. DMF was not only used as the solvent, but it also participated in the reaction as a component. Used as the cyanide sources, the aroyl cyanides solved the toxicity and solubility problems associated with the use of HCN or metal cyanides in the Strecker synthesis. This procedure furnished α‐amino‐α‐aryl carbonitriles in moderate to good yields with broad substrate scope. Moreover, this reaction could be performed under mild conditions with high atom economy.