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

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

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	637-641
Number of pages	5
Journal	Letters in Organic Chemistry
Volume	6
Issue number	8
DOIs	https://doi.org/10.2174/157017809790442916
Publication status	Published - Dec 2009

Keywords

Acyl cyanide
Asymmetric reduction
Catalysis
Cyanation
Cyanohydrin
Iodine
Lewis acids
Nitrile

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title = "ZnI2-catalyzed cyanation of acyl chlorides with TMS-CN: An interesting role of iodine",

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, Asymmetric reduction, Catalysis, Cyanation, Cyanohydrin, Iodine, Lewis acids, Nitrile",

author = "Wei Zeng and Jingya Yang and Bo Meng and Bo Zhang and Mingzhe Jiang and Chen, \{Fu Xue\}",

year = "2009",

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doi = "10.2174/157017809790442916",

language = "English",

volume = "6",

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journal = "Letters in Organic Chemistry",

issn = "1570-1786",

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T1 - ZnI2-catalyzed cyanation of acyl chlorides with TMS-CN

T2 - An interesting role of iodine

AU - Zeng, Wei

AU - Yang, Jingya

AU - Meng, Bo

AU - Zhang, Bo

AU - Jiang, Mingzhe

AU - Chen, Fu Xue

PY - 2009/12

Y1 - 2009/12

N2 - 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.

AB - 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.

KW - Acyl cyanide

KW - Asymmetric reduction

KW - Catalysis

KW - Cyanation

KW - Cyanohydrin

KW - Iodine

KW - Lewis acids

KW - Nitrile

UR - https://www.scopus.com/pages/publications/77249099808

U2 - 10.2174/157017809790442916

DO - 10.2174/157017809790442916

M3 - Article

AN - SCOPUS:77249099808

SN - 1570-1786

VL - 6

SP - 637

EP - 641

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 8

ER -

ZnI₂-catalyzed cyanation of acyl chlorides with TMS-CN: An interesting role of iodine

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Keywords

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