Issue 19, 2022

A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation

Abstract

General photoactivation of electron donor–acceptor (EDA) complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2.2]octane with visible light or natural sunlight was discovered. This practical and efficient mode enables the production of aryl radicals under mild conditions, providing an unrealized opportunity for two-step para-selective C–H functionalization of complex arenes. The novel mode for generating aryl radicals via an EDA complex was well supported by UV-vis absorbance measurements, nuclear magnetic resonance titration experiments, and density functional theory (DFT) calculations. The method was applied to the regio- and stereo-selective arylation of various N-heterocycles under mild conditions, yielding an assembly of challengingly linked heteroaryl–(hetero)aryl products. Remarkably, the meaningful couplings of bioactive molecules with structurally complex drugs or agricultural pharmaceuticals were achieved to display favorable in vitro antitumor activities, which will be of great value in academia or industry.

Graphical abstract: A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Mär 2022
Accepted
14 Apr 2022
First published
14 Apr 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-NC license

Chem. Sci., 2022,13, 5659-5666

A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation

K. Sun, A. Shi, Y. Liu, X. Chen, P. Xiang, X. Wang, L. Qu and B. Yu, Chem. Sci., 2022, 13, 5659 DOI: 10.1039/D2SC01241C

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