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, Fu-Xue Chen.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 8 , 2009

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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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Article Details

VOLUME: 6
ISSUE: 8
Year: 2009
Page: [637 - 641]
Pages: 5
DOI: 10.2174/157017809790442916
Price: $58

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