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

W Zeng, J Yang, B Meng, B Zhang…

Index: Zeng, Wei; Yang, Jingya; Meng, Bo; Zhang, Bo; Jiang, Mingzhe; Chen, Fu-Xue Letters in Organic Chemistry, 2009 , vol. 6, # 8 p. 637 - 641

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Citation Number: 4

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.