ZnI2-Catalyzed Cyanation of Acyl Chlorides with TMS-CN: An Interesting Role of Iodine
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; Lewis acids; asymmetric reduction; catalysis; cyanation; cyanohydrin; iodine; nitrile
Document Type: Research Article
Publication date: 01 December 2009
- Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
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