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Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles

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Abstract

The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C–C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon–carbon bonds sequentially.

Graphical abstract: Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles

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Publication details

The article was received on 19 Aug 2019, accepted on 30 Sep 2019 and first published on 09 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC04122B
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles

    J. Chen, S. Gao and M. Chen, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC04122B

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