Borane-Catalysed Hydroboration of Alkynes and Alkenes

Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

Simple, commercially available borane adducts, H₃B·THF and H₃B·SMe₂, have been used to catalyse the hydroboration of alkynes and alkenes with pinacolborane to give the alkenyl and alkyl boronic esters, respectively. Alkynes and terminal alkenes underwent highly regioselective hydroboration to give the linear boronic ester products. Good functional group tolerance was observed for substrates bearing ester, amine, ether and halide substituents. This catalytic process shows comparable reactivity to transition-metal-catalysed hydroboration protocols.

Key words

borane - hydroboration - alkynes - alkenes - main-group - catalysis

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