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Synlett 2003(13): 2095-2096  
DOI: 10.1055/s-2003-42031
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Trimethylsilyldiazomethane

Neil S. Hodnett*
School of Chemistry, University of Bristol, Cantocks Close, Bristol, BS8 1TS, UK
e-Mail: n.hodnett@bristol.ac.uk;
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Publication History

Publication Date:
08 October 2003 (online)

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Introduction

The commercially available reagent trimethylsilyldiazo­methane [1] can be used as a stable and safe alternative to ­diazomethane in one-carbon homologations, as in the Arndt-Eistert reaction, [2] the homologation of carbonyl compounds [3] [4] and O-methylation of carboxylic acids, phenols and alcohols. Additionally, the reagent can serve as a C-N-N synthon for the preparation of azoles.

Trimethylsilyldiazomethane is prepared as a hexane solution by diazo-transfer reaction between diphenyl phosphorazidate and the Grignard reagent prepared from chloromethyltrimethylsilane (Scheme 1). [5]