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

Wei      Zeng; Jingya      Yang; Bo      Meng; Bo      Zhang; Mingzhe      Jiang; Fu-Xue      Chen

doi:10.2174/157017809790442916

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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Letters in Organic Chemistry

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

Volume: 6 Issue: 8

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

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

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.

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Zeng Wei, Yang Jingya, Meng Bo, Zhang Bo, Jiang Mingzhe and Chen Fu-Xue, ZnI2-Catalyzed Cyanation of Acyl Chlorides with TMS-CN: An Interesting Role of Iodine, Letters in Organic Chemistry 2009; 6 (8) . https://dx.doi.org/10.2174/157017809790442916