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

Chem Sci. 2021 Aug 3;12(36):12174-12180. doi: 10.1039/d1sc02819g. eCollection 2021 Sep 22.

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.

PMID:34667583 | PMC:PMC8457391 | DOI:10.1039/d1sc02819g

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