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Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines
A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO(2) leading to consecutive double N-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457391/ https://www.ncbi.nlm.nih.gov/pubmed/34667583 http://dx.doi.org/10.1039/d1sc02819g |
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author | Maji, Subir Das, Arpan Mandal, Swadhin K. |
author_facet | Maji, Subir Das, Arpan Mandal, Swadhin K. |
author_sort | Maji, Subir |
collection | PubMed |
description | A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO(2) leading to consecutive double N-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles of N-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards double N-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations. |
format | Online Article Text |
id | pubmed-8457391 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-84573912021-10-18 Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines Maji, Subir Das, Arpan Mandal, Swadhin K. Chem Sci Chemistry A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO(2) leading to consecutive double N-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles of N-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards double N-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations. The Royal Society of Chemistry 2021-08-03 /pmc/articles/PMC8457391/ /pubmed/34667583 http://dx.doi.org/10.1039/d1sc02819g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Maji, Subir Das, Arpan Mandal, Swadhin K. Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title | Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title_full | Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title_fullStr | Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title_full_unstemmed | Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title_short | Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO(2) for consecutive N-methylation of amines |
title_sort | mesoionic n-heterocyclic olefin catalysed reductive functionalization of co(2) for consecutive n-methylation of amines |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457391/ https://www.ncbi.nlm.nih.gov/pubmed/34667583 http://dx.doi.org/10.1039/d1sc02819g |
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