Issue 14, 2022

Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation

Abstract

The reactivity of the sulfonyl group varies dramatically from nucleophilic sulfinates through chemically robust sulfones to electrophilic sulfonyl halides—a feature that has been used extensively in medicinal chemistry, synthesis, and materials science, especially as bioisosteric replacements and structural analogs of carboxylic acids and other carbonyls. Despite the great synthetic potential of the carboxylic to sulfonyl functional group interconversions, a method that can convert carboxylic acids directly to sulfones, sulfinates and sulfonyl halides has remained out of reach. We report herein the development of a photocatalytic system that for the first time enables direct decarboxylative conversion of carboxylic acids to sulfones and sulfinates, as well as sulfonyl chlorides and fluorides in one step and in a multicomponent fashion. A mechanistic study prompted by the development of the new method revealed the key structural features of the acridine photocatalysts that facilitate the decarboxylative transformations and provided an informative and predictive multivariate linear regression model that quantitatively relates the structural features with the photocatalytic activity.

Graphical abstract: Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation

Supplementary files

Article information

Article type
Edge Article
Submitted
08 fev 2022
Accepted
21 mar 2022
First published
21 mar 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, 4170-4179

Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation

V. T. Nguyen, G. C. Haug, V. D. Nguyen, N. T. H. Vuong, G. B. Karki, H. D. Arman and O. V. Larionov, Chem. Sci., 2022, 13, 4170 DOI: 10.1039/D2SC00789D

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