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Cp*Co(III)-catalyzed N-alkylation of amines with secondary alcohols

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Abstract

The hydrogen borrowing methodology is a well-known, environmentally benign method for the direct alkylation of amines and alcohols as it produces only water as a side product. However, the direct alkylation of amines with secondary alcohols using first-row transition metals is very challenging. We herein report for the first time Cp*Co(III)-catalyzed direct N-alkylation of amines starting from secondary alcohols. The reaction tolerates a wide variety of functional groups, including various aryl amines and amides. Our preliminary mechanistic investigations and DFT calculations suggest that [Cp*CoI2] is an active species, that PCy3 stabilizes the high-valent hydride intermediate, and that the reaction indeed proceeds through hydrogen auto-transfer processes.

Graphical abstract: Cp*Co(iii)-catalyzed N-alkylation of amines with secondary alcohols

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Publication details

The article was received on 28 Dec 2018, accepted on 07 Feb 2019 and first published on 08 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QO01389F
Citation: Org. Chem. Front., 2019, Advance Article

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    Cp*Co(III)-catalyzed N-alkylation of amines with secondary alcohols

    B. Emayavaramban, P. Chakraborty, E. Manoury, R. Poli and B. Sundararaju, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01389F

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