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

Joshua K. Mitchell; Waseem A. Hussain; Ajay H. Bansode; Ryan M. O’Connor; Dan E. Wise; Michael H. Choe; Marvin Parasram

doi:10.1021/acs.orglett.3c02292

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	6517-6521
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	35
DOIs	https://doi.org/10.1021/acs.orglett.3c02292
State	Published - Sep 8 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives",

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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T1 - Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives

AU - Mitchell, Joshua K.

AU - Hussain, Waseem A.

AU - Bansode, Ajay H.

AU - O’Connor, Ryan M.

AU - Wise, Dan E.

AU - Choe, Michael H.

AU - Parasram, Marvin

PY - 2023/9/8

Y1 - 2023/9/8

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AB - 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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JO - Organic Letters

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

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