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Copper‐Catalyzed Stereoselective Hydroarylation of 3‐Aryl‐2‐ propynenitriles with Arylboronic Acids
Author(s) -
Yamamoto Yoshihiko,
Asatani Tsuyoshi,
Kirai Naohiro
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900067
Subject(s) - chemistry , stereoselectivity , aryl , selectivity , copper , catalysis , methanol , combinatorial chemistry , anticancer drug , organic chemistry , drug , psychology , alkyl , psychiatry
The selective synthesis of 3,3‐diarylacrylonitriles has been achieved by copper‐catalyzed hydroarylation of 3‐aryl‐2‐propynenitriles with arylboronic acids. The starting cyanoalkynes were efficiently prepared from the appropriate aromatic aldehydes and diethyl cyanomethylphosphonate in two steps. The hydroarylation of the obtained cyanoalkyne substrates proceeded in methanol at ambient temperature to produce 3,3‐diarylacrylonitriles in good to high yields with excellent syn selectivity. The present method was successfully applied to the regiospecific synthesis of both stereoisomers of CC‐5079, which was recently reported as a potent anticancer drug.