Synlett 2012; 23(10): 1554-1555
DOI: 10.1055/s-0031-1290687
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© Georg Thieme Verlag Stuttgart · New York

Azidotrimethylsilane

Bao-Le Li
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, P. R. of China, Email: lible_111@163.com
› Author Affiliations
Further Information

Publication History

Publication Date:
29 May 2012 (online)

Introduction

Azidotrimethylsilane (TMSN3) is a clear, colorless, quite stable organosilane reagent and decomposes slowly even at 200 °C. It is considered a very convenient and safer replacement for hydrazoic acid as an azide source in many reactions.[ 1 ] It has been used for the synthesis of aryl 1,2,3-triazoles,[2] [3] [4] [5] tetrazoles,[ 6,7 ] functionalized bicyclic triazoles,[ 8 ] azides,[9] [10] [11] [12] [13] [14] [15] and N-tetrazolated diamine derivative.[ 16 ] In addition, azidotrimethylsilane has been employed for the preparation of proline-derived chiral aminotriazole ligands.[ 17 ] It was found to be a useful reagent for the aziridine ring opening to obtain azidomethyl-substituted pyrrole precursors,[ 18 ] or kinetic resolution of monosubstituted epoxide for the synthesis of optically pure 1-azido-2-trimethylsiloxyalkanes.[ 19 ]

Azidotrimethylsilane can be conveniently and rapidly prepared by adding chlorotrimethylsilane dropwise to a stirred solution of NaN3 in diethylene glycol dimethyl ether.[ 1 ]

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Scheme 1