Photocatalysis in Aqueous Micellar Media Enables Divergent C–H Arylation and N-Dealkylation of Benzamides

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Authors
Cybularczyk-Cecotka, Martyna
Predygier, Jędrzej
Crespi, Stefano
Szczepanik, Joanna
Giedyk, Maciej
Date
2022-03-04
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
Photocatalysis in aqueous micellar media has recently opened wide avenues to activate strong carbon−halide bonds. So far, however, it has mainly explored strongly reducing conditions, restricting the available chemical space to radical or anionic reactivity. Here, we demonstrate a controllable, photo catalytic strategy that channels the reaction of chlorinated benzamides via either a radical or a cationic pathway, enabling a chemodivergent C−H arylation or N-dealkylation. The catalytic system operates under mild conditions with methylene blue as a photocatalyst and blue LEDs as the light source. Factors determining the reactivity of substrates, their selectivity, and preliminary mechanistic studies are presented.
Description
Keywords
photocatalysis    divergence    micelles    aqueous solutions    aryl chlorides    benzamides    C−H arylation    dealkylation
Citation
ACS Catal. 2022, 12, 3543−3549. https://doi.org/10.1021/acscatal.2c00468
URI
https://open.icm.edu.pl/handle/123456789/21361
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