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Nickel-catalyzed alkyl–alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents

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Abstract

A novel nickel-catalyzed alkyl–alkyl cross coupling of non-activated secondary alkyl bromides with aldehydes via hydrazone intermediates has been developed. Aldehydes as alkyl carbanion equivalents replace traditional organometallic reagents. This coupling occurs on the carbon of the hydrazone rather than the nitrogen. In addition, non-activated primary and tertiary alkyl bromides also undergo the cross-coupling reaction to form new C(sp3)–C(sp3) bonds in moderate yields.

Graphical abstract: Nickel-catalyzed alkyl–alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents

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Publication details

The article was received on 13 Jan 2019, accepted on 30 Jan 2019 and first published on 31 Jan 2019


Article type: Communication
DOI: 10.1039/C9CC00307J
Citation: Chem. Commun., 2019, Advance Article

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    Nickel-catalyzed alkyl–alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents

    C. Zhu and J. Zhang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC00307J

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