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Photochemical benzylic radical arylation promoted by supported Pd nanostructures

Gawargy, Teresa A.; Costa, Paolo; Lanterna, Anabel E.; Scaiano, Juan C.

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Authors

Teresa A. Gawargy

Paolo Costa

Juan C. Scaiano



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.

Citation

Gawargy, T. A., Costa, P., Lanterna, A. E., & Scaiano, J. C. (2020). Photochemical benzylic radical arylation promoted by supported Pd nanostructures. Organic and Biomolecular Chemistry, 18(31), 6047-6052. https://doi.org/10.1039/d0ob01227k

Journal Article Type Article
Acceptance Date Jul 15, 2020
Online Publication Date Jul 16, 2020
Publication Date Aug 21, 2020
Deposit Date Jul 21, 2020
Publicly Available Date Jul 17, 2021
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 18
Issue 31
Pages 6047-6052
DOI https://doi.org/10.1039/d0ob01227k
Keywords Physical and Theoretical Chemistry; Organic Chemistry; Biochemistry
Public URL https://nottingham-repository.worktribe.com/output/4780000
Publisher URL https://pubs.rsc.org/en/Content/ArticleLanding/2020/OB/D0OB01227K#!divAbstract
Additional Information : This document is Similarity Check deposited; : Supplementary Information; : Single-blind; : Received 15 June 2020; Accepted 15 July 2020; Accepted Manuscript published 16 July 2020

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