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Issue 31, 2020
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Photochemical benzylic radical arylation promoted by supported Pd nanostructures

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Abstract

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.

Graphical abstract: Photochemical benzylic radical arylation promoted by supported Pd nanostructures

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Supplementary files

Article information


Submitted
15 Jun 2020
Accepted
15 Jul 2020
First published
16 Jul 2020

Org. Biomol. Chem., 2020,18, 6047-6052
Article type
Communication

Photochemical benzylic radical arylation promoted by supported Pd nanostructures

T. A. Gawargy, P. Costa, A. E. Lanterna and J. C. Scaiano, Org. Biomol. Chem., 2020, 18, 6047
DOI: 10.1039/D0OB01227K

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