A Safe and Scalable Procedure for Preparation of α-Picoline–Borane from Sodium Mono-acyloxyborohydrides and α-Picoline

Sodium monobenzoxyborohydride, which is easily prepared from sodium borohydride and benzoic acid in THF in situ, is treated with α-picoline in THF under mild conditions to give α-picoline–borane in an excellent yield. This method can be a practical preparation for α-picoline–borane.