Issue 36, 2021

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2 for consecutive N-methylation of amines

Abstract

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2 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.

Graphical abstract: Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2 for consecutive N-methylation of amines

Supplementary files

Article information

Article type
Edge Article
Submitted
24 May 2021
Accepted
02 Aug 2021
First published
03 Aug 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 12174-12180

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2 for consecutive N-methylation of amines

S. Maji, A. Das and S. K. Mandal, Chem. Sci., 2021, 12, 12174 DOI: 10.1039/D1SC02819G

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