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 des. 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements