Substitution at sp³ boron of a six-membered NHC·BH₃: convenient access to a dihydroxyborenium cation

Abstract

Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I₂ led to NHC boryl iodides, 6-SIDipp·BH₂I (2) and 6-SIDipp·BHI₂ (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO₂ (5 and 7) functional groups. The addition of Br₂/H₂O to 1 smoothly results in a dihydroxyborenium cation (8).