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Copper‐Photocatalyzed Hydroboration of Alkynes and Alkenes

Mingbing Zhong, Yohann Gagné, Taylor O. Hope, Xavier Pannecoucke, Mathieu Frenette, Philippe Jubault, Thomas Poisson

2021Angewandte Chemie18 citationsDOIOpen Access PDF

Abstract

Abstract The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly‐designed copper photocatalysts with B 2 Pin 2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and alkynes. The hydroborated products were isolated in high yields, with excellent diastereoselectivities and a high functional group tolerance under mild conditions. The hydroboration reactions were developed under continuous flow conditions to demonstrate their synthetic utility. The reaction mechanism was studied and suggested an oxidation reaction between an in situ formed borate and the Cu‐photocatalyst in its excited state for the boryl radical formation.

Topics & Concepts

HydroborationChemistryPhotocatalysisCopperBoronRadicalFlow chemistryContinuous flowPhotochemistryFunctional groupOrganic chemistryCatalysisMechanicsPhysicsPolymerRadical Photochemical ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods