Photocatalyst-free, visible-light-mediated C(sp3)-H arylation of amides via a solvent-caged EDA complex

Kaur, Jaspreet and Shahin, Ahmed and Barham, Joshua P. (2021) Photocatalyst-free, visible-light-mediated C(sp3)-H arylation of amides via a solvent-caged EDA complex. Organic Letters, 23 (6). pp. 2002-2006. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.1c00132)

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Abstract

A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

ORCID iDs

Kaur, Jaspreet, Shahin, Ahmed and Barham, Joshua P. ORCID logoORCID: https://orcid.org/0000-0003-1675-9399;