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

[Image: see text] 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...

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Autores principales: Mitchell, Joshua K., Hussain, Waseem A., Bansode, Ajay H., O’Connor, Ryan M., Wise, Dan E., Choe, Michael H., Parasram, Marvin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496125/
https://www.ncbi.nlm.nih.gov/pubmed/37680131
http://dx.doi.org/10.1021/acs.orglett.3c02292
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author Mitchell, Joshua K.
Hussain, Waseem A.
Bansode, Ajay H.
O’Connor, Ryan M.
Wise, Dan E.
Choe, Michael H.
Parasram, Marvin
author_facet Mitchell, Joshua K.
Hussain, Waseem A.
Bansode, Ajay H.
O’Connor, Ryan M.
Wise, Dan E.
Choe, Michael H.
Parasram, Marvin
author_sort Mitchell, Joshua K.
collection PubMed
description [Image: see text] 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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spelling pubmed-104961252023-09-13 Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives Mitchell, Joshua K. Hussain, Waseem A. Bansode, Ajay H. O’Connor, Ryan M. Wise, Dan E. Choe, Michael H. Parasram, Marvin Org Lett [Image: see text] 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. American Chemical Society 2023-08-24 /pmc/articles/PMC10496125/ /pubmed/37680131 http://dx.doi.org/10.1021/acs.orglett.3c02292 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Mitchell, Joshua K.
Hussain, Waseem A.
Bansode, Ajay H.
O’Connor, Ryan M.
Wise, Dan E.
Choe, Michael H.
Parasram, Marvin
Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title_full Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title_fullStr Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title_full_unstemmed Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title_short Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
title_sort photoinduced nitroarenes as versatile anaerobic oxidants for accessing carbonyl and imine derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496125/
https://www.ncbi.nlm.nih.gov/pubmed/37680131
http://dx.doi.org/10.1021/acs.orglett.3c02292
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