Issue 31, 2020

Photochemical benzylic radical arylation promoted by supported Pd nanostructures

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

Supplementary files

Article information

Article type
Communication
Submitted
15 Jun 2020
Accepted
15 Jul 2020
First published
16 Jul 2020

Org. Biomol. Chem., 2020,18, 6047-6052

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements