Issue 39, 2022

Visible-light-induced indole synthesis via intramolecular C–N bond formation: desulfonylative C(sp2)–H functionalization

Abstract

Despite significant advances made on the synthesis of indole derivatives through photochemical strategies during the past several years, the requirement of equivalent amounts of oxidants, bases or other additional additives has limited their practical applications in the synthesis of natural products and pharmaceuticals as environment-friendly processes. Herein, we report LED visible-light-induced redox neutral desulfonylative C(sp2)–H functionalization for the synthesis of N-substituted indoles with a broad scope through γ-fragmentation under mild conditions in the absence of any additional additive. The reaction mechanism paradigm has been investigated on the basis of deuterium labeling experiments, kinetic analysis, Hammett plotting analysis and DFT calculations.

Graphical abstract: Visible-light-induced indole synthesis via intramolecular C–N bond formation: desulfonylative C(sp2)–H functionalization

Supplementary files

Article information

Article type
Edge Article
Submitted
20 May 2022
Accepted
15 Sep 2022
First published
16 Sep 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 11623-11632

Visible-light-induced indole synthesis via intramolecular C–N bond formation: desulfonylative C(sp2)–H functionalization

Q. Li, X. Gu, Y. Wei and M. Shi, Chem. Sci., 2022, 13, 11623 DOI: 10.1039/D2SC02822K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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