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Efficient and Versatile Catalytic Systems for the N-Methylation of Primary Amines with Methanol Catalyzed by N-Heterocyclic Carbene Complexes of Iridium

Genki Toyooka, Akiko Tuji, Ken-ichi Fujita*

*Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Email:

G. Toyooka, A. Tuji, K.-i. Fujita, Synthesis, 2018, 50, 4617-4626.

DOI: 10.1055/s-0037-1610252

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Iridium complexes bearing an N-heterocyclic carbene (NHC) ligand exhibited high catalytic performance for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures. For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished.

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Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for N,N-Dimethylamine Derivatives

J. Jeong, K.-i. Fujita, J. Org. Chem., 2021, 86, 4053-4060.

Key Words

iridium, carbene ligands, hydrogen transfer, aryl amines, alkylation, methylation

ID: J66-Y2018