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Cobalt-catalyzed direct transformation of aldehydes to esters: the crucial role of an enone as a mediator

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Abstract

An oxidative esterification of aldehydes with alkanols catalyzed by an in situ generated low-valent cobalt system has been developed using an enone as a mild oxidant. Mechanistic studies revealed that it proceeds through a Co(I)-catalyzed hydrogen-transfer route, wherein the α-vinyl moiety in the bidentate enone functions as a hydride acceptor. Meanwhile, Co(I)-catalyzed formyl C–H activation occurred as a competing reaction leading to aldehyde dimerization. The occurrence of the usually kinetically disfavored hydride transfer step therein was significantly increased in the presence of an enone reacting as a hydride transfer initiator.

Graphical abstract: Cobalt-catalyzed direct transformation of aldehydes to esters: the crucial role of an enone as a mediator

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Publication details

The article was received on 03 Dec 2018, accepted on 23 Jan 2019 and first published on 25 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01298A
Citation: Org. Chem. Front., 2019, Advance Article

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    Cobalt-catalyzed direct transformation of aldehydes to esters: the crucial role of an enone as a mediator

    B. Jiang, Y. Lin, M. Wang, D. Liu, B. Xu and S. Zhang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01298A

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