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A pincer ligand enabled ruthenium catalyzed highly selective N-monomethylation of nitroarenes with methanol as the C1 source

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Abstract

A straightforward and highly selective N-monomethylation of nitro compounds with methanol as the C1 source was developed by employing [RuCl2(p-cymene)2]2 as the catalyst and an NNN pincer (amine-pyridine-imine, API) as the ligand. This protocol was found to be highly selective and effective in the N-monomethylation of a broad spectrum of nitroarenes including pharmaceutically relevant nitro compounds with good tolerance of a set of functional groups. The mechanistic studies revealed that the reaction proceeded via a borrowing-hydrogen pathway in a one-pot cascade manner and methanol serves as both a hydrogen source and a methylation agent.

Graphical abstract: A pincer ligand enabled ruthenium catalyzed highly selective N-monomethylation of nitroarenes with methanol as the C1 source

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Publication details

The article was received on 26 Apr 2019, accepted on 09 Jun 2019 and first published on 11 Jun 2019


Article type: Research Article
DOI: 10.1039/C9QO00544G
Org. Chem. Front., 2019, Advance Article

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    A pincer ligand enabled ruthenium catalyzed highly selective N-monomethylation of nitroarenes with methanol as the C1 source

    S. Zhang, J. J. Ibrahim and Y. Yang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00544G

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