Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 10, 2020
Previous Article Next Article

Effective N-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach to N-methyl amines

Author affiliations

Abstract

Compound [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] featuring a flexible pyridine/OMe functionalized NHC ligand κ1C coordinated efficiently catalyzes the selective N-monomethylation of nitroarenes using methanol as both the reducing agent and the C1 source. A range of functionalized nitroarenes including heterocyclic or sterically hindered derivatives have been efficiently converted to the corresponding N-monomethyl amines in good yields at low catalyst loadings using sub-stoichiometric amounts of Cs2CO3 as a base. Mechanistic investigations support a borrowing-hydrogen mechanism in which methanol acts as the hydrogen source and methylating agent. Further, the hydrogen transfer reduction of nitrobenzene to aniline under optimized reaction conditions should proceed through a direct mechanism involving nitrosobenzene and N-phenylhydroxylamine intermediates.

Graphical abstract: Effective N-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach to N-methyl amines

Back to tab navigation

Supplementary files

Article information


Submitted
07 Apr 2020
Accepted
30 Apr 2020
First published
01 May 2020

Catal. Sci. Technol., 2020,10, 3458-3467
Article type
Paper

Effective N-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach to N-methyl amines

M. González-Lainez, M. V. Jiménez, V. Passarelli and J. J. Pérez-Torrente, Catal. Sci. Technol., 2020, 10, 3458
DOI: 10.1039/D0CY00707B

Social activity

Search articles by author

Spotlight

Advertisements