Facile preparation of alpha-aryl nitriles by direct cyanation of alcohols with TMSCN under the catalysis of InX3

Gang Chen; Zheng Wang; Jiang Wu; Kuiling Ding

doi:10.1021/ol801812a

Facile preparation of alpha-aryl nitriles by direct cyanation of alcohols with TMSCN under the catalysis of InX3

Org Lett. 2008 Oct 16;10(20):4573-6. doi: 10.1021/ol801812a. Epub 2008 Sep 23.

Authors

Gang Chen¹, Zheng Wang, Jiang Wu, Kuiling Ding

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

PMID: 18808133
DOI: 10.1021/ol801812a

Abstract

A convenient and efficient synthesis of alpha-aryl nitriles was developed by direct cyanation of alcohols with TMSCN under the catalysis of Lewis acid. Using 5-10 mol % of InBr3 as the catalyst, a variety of benzylic alcohols can be converted to the corresponding nitriles in 5-30 min with yields of 46-99%.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Bromine Compounds / chemistry*
Catalysis
Cyanides / chemistry*
Furans / chemistry*
Indium / chemistry*
Molecular Structure
Nitriles / chemistry*
Trimethylsilyl Compounds / chemistry*

Substances

Alcohols
Bromine Compounds
Cyanides
Furans
Nitriles
Trimethylsilyl Compounds
Indium
trimethylsilyl cyanide