N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions

Herein, we disclose an NHC-catalyzed aerobic oxidation of unactivated aldimines for the synthesis of amides via umpolung of imines proceeding through an aza-Breslow intermediate. We have developed an eco-friendly method for the conversion of imines to amides by using molecular oxygen in air as the s...

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Autores principales: Ramarao, Jakkula, Yadav, Sanjay, Satyam, Killari, Suresh, Surisetti
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982222/
https://www.ncbi.nlm.nih.gov/pubmed/35424774
http://dx.doi.org/10.1039/d2ra00897a
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author Ramarao, Jakkula
Yadav, Sanjay
Satyam, Killari
Suresh, Surisetti
author_facet Ramarao, Jakkula
Yadav, Sanjay
Satyam, Killari
Suresh, Surisetti
author_sort Ramarao, Jakkula
collection PubMed
description Herein, we disclose an NHC-catalyzed aerobic oxidation of unactivated aldimines for the synthesis of amides via umpolung of imines proceeding through an aza-Breslow intermediate. We have developed an eco-friendly method for the conversion of imines to amides by using molecular oxygen in air as the sole oxidant and dimethyl carbonate (DMC) as a green solvent under mild reaction conditions. Broad substrate scope, high yields and gram scale syntheses expand the practicality of the developed method.
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spelling pubmed-89822222022-04-13 N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions Ramarao, Jakkula Yadav, Sanjay Satyam, Killari Suresh, Surisetti RSC Adv Chemistry Herein, we disclose an NHC-catalyzed aerobic oxidation of unactivated aldimines for the synthesis of amides via umpolung of imines proceeding through an aza-Breslow intermediate. We have developed an eco-friendly method for the conversion of imines to amides by using molecular oxygen in air as the sole oxidant and dimethyl carbonate (DMC) as a green solvent under mild reaction conditions. Broad substrate scope, high yields and gram scale syntheses expand the practicality of the developed method. The Royal Society of Chemistry 2022-03-08 /pmc/articles/PMC8982222/ /pubmed/35424774 http://dx.doi.org/10.1039/d2ra00897a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ramarao, Jakkula
Yadav, Sanjay
Satyam, Killari
Suresh, Surisetti
N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title_full N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title_fullStr N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title_full_unstemmed N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title_short N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
title_sort n-heterocyclic carbene (nhc)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982222/
https://www.ncbi.nlm.nih.gov/pubmed/35424774
http://dx.doi.org/10.1039/d2ra00897a
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AT satyamkillari nheterocycliccarbenenhccatalyzedoxidationofunactivatedaldiminestoamidesviaimineumpolungunderaerobicconditions
AT sureshsurisetti nheterocycliccarbenenhccatalyzedoxidationofunactivatedaldiminestoamidesviaimineumpolungunderaerobicconditions

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