Issue 8, 2024

Unprecedented single-electron-transfer reduction-based N → C acyl migration reactions of imides enabled by redox-neutral photocatalysis

Abstract

Herein, we report new redox-neutral photoredox-catalyzed acyl migration reactions based on a reductive radical-polar crossover process for the first time. Using alkyl silicates as radical precursors, a range of enamides bearing various functional groups are shown to be effective radical acceptors for these transformations. Under mild photocatalytic conditions, various α-amino ketones were efficiently prepared, which are precursors of primary α-tertiary amines. Mechanistic studies suggest that a radical addition/single-electron-transfer reduction/acyl migration cascade process was involved. This novel SET reduction-based acyl migration reaction features base-, additive-, and exogenous reductant-free conditions.

Graphical abstract: Unprecedented single-electron-transfer reduction-based N → C acyl migration reactions of imides enabled by redox-neutral photocatalysis

Supplementary files

Article information

Article type
Research Article
Submitted
24 Nov 2023
Accepted
17 Feb 2024
First published
19 Feb 2024

Org. Chem. Front., 2024,11, 2344-2350

Unprecedented single-electron-transfer reduction-based N → C acyl migration reactions of imides enabled by redox-neutral photocatalysis

L. Huai, L. Zhang, Z. Wang and Y. Fang, Org. Chem. Front., 2024, 11, 2344 DOI: 10.1039/D3QO01955A

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