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Nickel-catalyzed hydroalkylation and hydroalkenylation of 1,3-dienes with hydrazones

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Abstract

Transition-metal-catalyzed hydrofunctionalization of 1,3-dienes is a useful and atom-economical method for constructing allylic compounds. Although substantial progress on hydroalkylation of dienes with stabilized carbon nucleophiles has been made, hydroalkylation of dienes with unstabilized carbon nucleophiles has remained a challenge. In this article, we report a protocol for nickel-catalyzed hydroalkylation of dienes with hydrazones, which serve as equivalents of alkyl carbon nucleophiles. In addition, we developed a protocol for hydroalkenylation of dienes with α,β-unsaturated hydrazones, providing a new method for the synthesis of 1,4-dienes. These hydroalkylation and hydroalkenylation reactions feature mild conditions and a wide substrate scope, and the utility of the reaction products is demonstrated by the preparation of an activator of soluble guanylate cyclase.

Graphical abstract: Nickel-catalyzed hydroalkylation and hydroalkenylation of 1,3-dienes with hydrazones

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Publication details

The article was received on 21 Aug 2019, accepted on 19 Sep 2019 and first published on 27 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC04177J
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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    Nickel-catalyzed hydroalkylation and hydroalkenylation of 1,3-dienes with hydrazones

    L. Cheng, M. Li, B. Wang, L. Xiao, J. Xie and Q. Zhou, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC04177J

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