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

Yi-Zhou Zhan, Nan Xiao and Wei Shu ()
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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

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-21083-w

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