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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

ZnI2-Catalyzed Cyanation of Acyl Chlorides with TMS-CN: An Interesting Role of Iodine

Author(s): Wei Zeng, Jingya Yang, Bo Meng, Bo Zhang, Mingzhe Jiang and Fu-Xue Chen

Volume 6, Issue 8, 2009

Page: [637 - 641] Pages: 5

DOI: 10.2174/157017809790442916

Price: $65

Abstract

Both aliphatic and aromatic acyl cyanides have been synthesized with TMSCN and acyl chloride with ZnI2 (0.5 mol%). However the in situ generated I2 is proposed accounting for the formation of by-product O-TMS enolate at high catalyst loading rather than 0.5 mol%. Asymmetric reduction of benzoyl cyanide with borane has been explored in 82% yield and 24% ee.

Keywords: Acyl cyanide, catalysis, cyanation, iodine, Lewis acids, nitrile, cyanohydrin, asymmetric reduction


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