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Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer

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Abstract

A cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling reaction between an aryl imine and a 2-bromobenzyl-protected secondary amine is reported. Promoted by a combination of a cobalt–N-heterocyclic carbene catalyst and a Grignard reagent, the reaction allows for the introduction of α-aminoalkyl groups into the ortho position of the imine at a mild temperature. The cobalt catalyst is proposed to play key roles in two distinct modes of C–H cleavage, i.e., directed C–H metalation and 1,5-hydrogen atom transfer (HAT).

Graphical abstract: Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer

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Publication details

The article was received on 04 Oct 2017, accepted on 01 Nov 2017 and first published on 02 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00906B
Citation: Org. Chem. Front., 2018, Advance Article
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    Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer

    Q. Sun and N. Yoshikai, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00906B

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