Journal
CHEMICAL SCIENCE
Volume 12, Issue 36, Pages 12174-12180Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc02819g
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Funding
- STARS Program of India [MoE-STARS/STARS-1/473]
- CSIR, Delhi [09/921(0233)/2019-EMR-I]
- IISER Kolkata
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A new catalyst was introduced for the reductive functionalization of CO2 leading to consecutive double N-methylation of primary amines. The catalyst showed high efficiency in methylating a wide range of secondary and primary amines under mild conditions. Detailed mechanistic cycle was proposed through a series of control reactions and structural studies.
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.
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