Issue 13, 2023

Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes

Abstract

Recently, photochemistry of Electron Donor–Acceptor (EDA) complexes employing catalytic amounts of electron donors have become of interest as a new methodology in the catalysis field, allowing for decoupling of the electron transfer (ET) from the bond-forming event. However, examples of practical EDA systems in the catalytic regime remain scarce, and their mechanism is not yet well-understood. Herein, we report the discovery of an EDA complex between triarylamines and α-perfluorosulfonylpropiophenone reagents, catalyzing C–H perfluoroalkylation of arenes and heteroarenes under visible light irradiation in pH- and redox-neutral conditions. We elucidate the mechanism of this reaction using a detailed photophysical characterization of the EDA complex, the resulting triarylamine radical cation, and its turnover event.

Graphical abstract: Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Dec 2022
Accepted
12 Feb 2023
First published
14 Mar 2023
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., 2023,14, 3470-3481

Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes

D. J. Castillo-Pazos, J. D. Lasso, E. Hamzehpoor, J. Ramos-Sánchez, J. M. Salgado, G. Cosa, D. F. Perepichka and C. Li, Chem. Sci., 2023, 14, 3470 DOI: 10.1039/D2SC07078B

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