Issue 9, 2023

Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

Abstract

The development of strategies for single and selective C–F bond activation represents an important avenue to overcome limitations in the synthesis of valuable fluorine-containing compounds. The synthetic and medicinal research communities would benefit from new routes that access such relevant molecules in a simple manner. Herein we disclose a straightforward and mechanistically distinct pathway to generate gem-difluoromethyl radicals and their installation onto N-arylmethacrylamides for the preparation of valuable difluorinated oxindole derivatives. To achieve operational simplicity, the use of a readily available benzenethiol as a photocatalyst under open-to-air conditions was developed, demonstrating the facile multigram preparation of the targeted fluorinated molecules. Additionally, dispersion-corrected density functional theory (DFT) and empirical investigations provide a new basis to support the proposed reaction pathway, indicating that arene thiolate is an efficient organophotocatalyst for this transformation.

Graphical abstract: Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Nov. 2022
Accepted
02 Febr. 2023
First published
09 Febr. 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, 2379-2385

Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

B. Matsuo, J. Majhi, A. Granados, M. Sharique, R. T. Martin, O. Gutierrez and G. A. Molander, Chem. Sci., 2023, 14, 2379 DOI: 10.1039/D2SC06179A

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