Photochemical benzylic radical arylation promoted by supported Pd nanostructures.

Org Biomol Chem

Department of Chemistry and Biomolecular Sciences and Centre for Advanced Materials Research (CAMaR), University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.

Published: August 2020

We report a novel way to promote photochemical benzylic radical arylations using Pd nanostructures. Traditional benzylic radical reaction pathways are challenged by the presence of metal centres that provoke unprecedented regioselectivity towards more synthetically relevant C(sp3)-C(sp2) couplings. This new C-H activation pathway is rationalised by means of a pseudo-persistent radical effect facilitated by metal centres. We show the mechanistic and computational aspects of the heterogeneous photocatalytic processes that are the root of this drastic change in reactivity.

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http://dx.doi.org/10.1039/d0ob01227kDOI Listing

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