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Benzylic C–H heteroarylation of N-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer

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Abstract

A visible light initiated α-C(sp3)–H arylation of N-(benzyloxy)phthalimides with cyanopyridines for the construction of highly valuable pyridinyl-containing diarylmethanols, including bioactive motif-based analogues, is reported. This method enables arylation of the C(sp3)–H bonds adjacent to an oxygen atom through alkoxy radical formation by O–N bond cleavage, 1,2-hydrogen atom transfer (HAT), arylation and C–CN bond cleavage cascades, and offers a means to exploit 1,2-HAT modes to incorporate functional groups for constructing functionalized alcohols.

Graphical abstract: Benzylic C–H heteroarylation of N-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer

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Article information


Submitted
21 May 2020
Accepted
22 Jun 2020
First published
22 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Benzylic C–H heteroarylation of N-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer

L. Zhong, H. Wang, X. Ouyang, J. Li and D. An, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03619F

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