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Updated: Mar 28, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Cobalt-Catalyzed N-Alkylation of Amines with Alcohols
Guoqi Zhang1, Zhiwei Yin1,2, Shengping Zheng2
1Department of Sciences, John Jay College and Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , New York, New York 10019, United States.
Abstract:
A well-defined nonprecious metal cobalt(II) catalyst based on a pincer PNP ligand has been employed for the efficient N-alkylation of both aromatic and aliphatic amines with alcohols. A subtle change of reaction conditions (simply adding 4 Å molecular sieves) was observed to readily switch the resulting products (amines vs imines) with high chemoselectivity. A range of alcohols and amines including both aromatic and aliphatic substrates were efficiently converted to secondary amines in good-to-excellent yields when 2 mol % cobalt catalyst was used. Additional experiments indicate that a hydrogen-borrowing mechanism is responsible for the tandem acceptorless dehydrogenation/condensation/hydrogenation process.
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