Azidotrimethylsilane

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 ]

Scheme 1

• References

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