Efficient O-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions

D Amantini, F Fringuelli, F Pizzo…

Index: Amantini; Fringuelli; Pizzo; Vaccaro Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6734 - 6737

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Citation Number: 69

Abstract

A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol%) of tetrabutylammonium bromide (TBABr) at 30 or 70° C. Under catalytic conditions, the yields of the corresponding ...

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