Trimethylsilyldiazomethane

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]

References

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