Palladium-catalyzed borylation of primary alkyl bromides

Abstract

A mild Pd-catalyzed process for the borylation of alkyl bromides has been developed using bis(pinacolato)diboron as a boron source. This process accommodates the use of a wide range of functional groups on the alkyl bromide substrate. Primary bromides react with complete selectivity in the presence of a secondary bromide. The generality of this approach is demonstrated by its extension to the use of alkyl iodides and alkyl tosylates, as well as borylation reactions employing bis(neopentyl glycolato)diboron as the boron source.

Scheme 1

Selective Borylation of Primary Bromidea ^a Alkyl bromide (1 mmol), bis(pinacolato)diboron (1.2 mmol); average yield of 2 runs.