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Copper‐Mediated Cyanation of Aryl Halides by Activation of Benzyl Cyanide as the Cyanide Source
Author(s) -
Wen Qiaodong,
Jin Jisong,
Mei Yuncai,
Lu Ping,
Wang Yanguang
Publication year - 2013
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.201300052
Subject(s) - cyanation , chemistry , aryl , cyanide , halide , reagent , bond cleavage , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl
Aryl nitriles were efficiently synthesized through copper‐mediated cyanation of aryl halides using benzyl cyanide as the cyanide source. Aryl halides with various substituents on the aromatic ring afforded the corresponding aryl nitriles in 32–97 % yields (25 examples). This reaction could also be carried on a gram scale by using commercially available reagents. Additionally, a C–H bond oxidation and a C–CN cleavage are proposed to be involved in this cascade process.