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. 2023 Sep 8;25(35):6517-6521.
doi: 10.1021/acs.orglett.3c02292. Epub 2023 Aug 24.

Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives

Joshua K Mitchell  1 , Waseem A Hussain  1 , Ajay H Bansode  1 , Ryan M O'Connor  1 , Dan E Wise  1 , Michael H Choe  1 , Marvin Parasram  1
Affiliations

Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives

Joshua K Mitchell et al. Org Lett. .

Abstract

Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support the idea that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide the respective ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom transfer (OAT) events occur to yield carboxylic acids and amides, respectively. This transformation is amenable to a continuous-photoflow setup, which led to reduced reaction times.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Prior Methods and Hypothesized Work
Scheme 2
Scheme 2. Continuous-Photoflow Oxidations
Scheme 3
Scheme 3. Proposed Mechanism
See this image and copyright information in PMC

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