Radical-polar crossover reactions of vinylboron ate complexes

Abstract

Boron choreographs a double reaction In the widely used Suzuki coupling reaction, boron surrenders an olefinic substituent to a metal catalyst en route to carbon-carbon bond formation. Kischkewitz et al. report a metal-free alternative pathway, wherein the boron stays bound to one end of the olefin while a carbon radical attacks the other end. Charge transfer then prompts migration of an alkyl or aryl group from the boron to form a second carbon-carbon bond. The boron can subsequently be displaced, generating a versatile array of alcohols, lactones, and quaternary carbon centers from simple precursors. Science , this issue p. 936