Catalysis

Micellar photocatalysis enables divergent C-H arylation and N dealkylation of benzamides via N-acyliminium cations

Authors

Abstract

Micellar photocatalysis has recently opened new 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 radical-polar crossover process involving cationic intermediates, which enables chemodivergent modification of chlorinated benzamide derivatives via either C H arylation or N dealkylation. The catalytic system operates under mild conditions employing methylene blue as a photocatalyst and blue LEDs as the light source. Factors determining the reactivity of substrates and preliminary mechanistic studies are presented.

Version notes

The research was extended to include additional optimization, mechanistic and control experiments. Computational analysis was performed. The proposed mechanism was adapted in line with the new data. The manuscript was rewritten and SI was corrected.

Content

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Supplementary material

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Supporting Information
Supporting Information for "Micellar photocatalysis enables divergent C-H arylation and N dealkylation of benzamides via N-acyliminium cations"