Synthesis 2006(16): 2649-2652  
DOI: 10.1055/s-2006-942483
PAPER
© Georg Thieme Verlag Stuttgart · New York

Construction of Tetrasubstituted Carbon by an Organocatalyst: Cyanation Reaction of Ketones and Ketimines Catalyzed by a Nucleophilic N-Heterocyclic Carbene

Yoshimasa Fukuda, Kazuhiro Kondo*, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
Fax: +81(52)8363439; e-Mail: kazuk@phar.nagoya-cu.ac.jp; e-Mail: aoyama@phar.nagoya-cu.ac.jp;
Further Information

Publication History

Received 10 March 2006
Publication Date:
12 July 2006 (eFirst)

Abstract

A method for cyanation reaction of ketones and ketimines having lower reactivity than aldehydes and aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and potassium tert-butoxide, as a nucleophilic organocatalyst, is described. These cyanations of ketones and ketimines afford the corresponding products in good yields under mild reaction conditions.

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4

We have already found that DMF is a good solvent for accelerating the cyanation of aldehydes and aldimines. See ref. 2.