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

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 ?,?-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.

SUBMITTER: Cheng L

PROVIDER: S-EPMC6988744 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Cheng Lei L Li Ming-Ming MM Wang Biao B Xiao Li-Jun LJ Xie Jian-Hua JH Zhou Qi-Lin QL

Chemical science 20190927 44

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 ...[more]

PMID: 32110333

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