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Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

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  • Yi-Zhou Zhan

    (and Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology)

  • Nan Xiao

    (and Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology)

  • Wei Shu

    (and Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology)

Abstract

The development of straightforward synthesis of regio- and stereodefined alkenes with multiple aliphatic substituents under mild conditions is an unmet challenge owing to competitive β-hydride elimination and selectivity issues. Herein, we report the nickel-catalyzed intermolecular cross-dialkylation of alkynes devoid of directing or activating groups to afford multiple aliphatic substituted alkenes in a syn-selective fashion at room temperature. The combination of two-electron oxidative cyclometallation and single-electron cross-electrophile coupling of nickel enables the syn-cross-dialkylation of alkynes at room temperature. This reductive protocol enables the sequential installation of two different alkyl substituents onto alkynes in a regio- and stereo-selective manner, circumventing the tedious preformation of sensitive organometallic reagents. The synthetic utility of this protocol is demonstrated by efficient synthesis of multi-substituted unfunctionalized alkenes and diverse transformations of the product.

Suggested Citation

  • Yi-Zhou Zhan & Nan Xiao & Wei Shu, 2021. "Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-21083-w
    DOI: 10.1038/s41467-021-21083-w
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