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Issue 22, 2020
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Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement via C(Ar)–O bond cleavage

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Abstract

The use of photochemical reactions that do not require expensive photocatalysts or transition metals is an environmentally friendly strategy for accomplishing a variety of structural transformations. Herein, we report a protocol for photoinduced transition-metal- and external-photocatalyst-free intramolecular heteroaryl/aryl rearrangement reactions of 2-heteroaryl/aryloxybenzaldehydes. The protocol was compatible with a variety of functionalities, including methyl, methoxy, cyano, ester, trifluoromethyl, halogen, and heteroaromatic rings. Control experiments suggested that the reaction proceeded via a photoinduced intramolecular heteroaryl/aryl rearrangement process involving photoexcitation of the aldehyde carbonyl group, radical addition, C–C bond formation and C(Ar)–O bond cleavage.

Graphical abstract: Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement via C(Ar)–O bond cleavage

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Supplementary files

Article information


Submitted
17 Mar 2020
Accepted
14 May 2020
First published
26 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5740-5744
Article type
Edge Article

Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement via C(Ar)–O bond cleavage

Q. Dou, C. Li and H. Zeng, Chem. Sci., 2020, 11, 5740 DOI: 10.1039/D0SC01585G

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