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Synlett 2007(10): 1625-1626  
DOI: 10.1055/s-2007-982537
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© Georg Thieme Verlag Stuttgart · New York

Trimethylsilyl Cyanide (TMSCN)

Ebrahim Soleimani*
Department of Chemistry, Shahid Beheshti University, P. O. Box 19396-4716, Tehran, Iran
e-Mail: e_soleimani@sbu.ac.ir;
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Publication History

Publication Date:
06 June 2007 (online)

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Introduction

Cyanation of carbonyl compounds is one of the most ­powerful procedures for the synthesis of polyfunctionalized molecules. Compared to various cyanating reagents such as KCN, NaCN, and HCN, trimethylsilyl cyanide (TMSCN) is a safer and more effective cyanide source for nucleophilic addition to carbonyl compounds under mild conditions. [1] [2] Asymmetric addition of TMSCN to carbonyl compounds and subsequent hydrolysis produces chiral cyanohydrins. [3] The reaction of an epoxide with TMSCN leads to formation of either trimethylsilyloxy ­nitrile (C-nucleophilic attack) or trimethylsiloxy iso­cyanide (N-nucleophilic attack) depending on the nature of the catalyst, due to the ambident nucleophilic character of TMSCN. [4] Cyanation of nucleophilic alkynes as an easy approach to substituted α-cyanoenamines is another ­ability of TMSCN. [5] Recently, TMSCN was used as a functional, yet non-classical isonitrile, for the synthesis of 3-aminoimidazo[1,2-a]pyridines. [6]