PAPER	Synthesis 2006: 405-410   DOI: 10.1055/s-2005-918517
© Georg Thieme Verlag Stuttgart · New York
A Convenient Method for the Preparation of Benzyl Isocyanides
Yoshikazu Kitano*, Tetsuya Manoda, Teppei Miura, Kazuhiro Chiba, Masahiro Tada
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan Fax: +81(42)3608830; e-Mail: kitayo@cc.tuat.ac.jp;
Received 4 July 2005

Abstract

Treatment of benzyl halides with silver salts (AgClO₄, AgBF₄, or AgOTf) and trimethylsilyl cyanide (TMSCN) in CH₂Cl₂ followed by cleavage of the carbon-silicon bond with aqueous NaHCO₃ or TBAF directly afforded the corresponding isocyanides.

Key words

benzyl isocyanides - benzyl halides - silver salts - tri­methylsilyl cyanide - perchlorate