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Issue 44, 2019
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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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Supplementary files

Article information


Submitted
21 Aug 2019
Accepted
19 Sep 2019
First published
27 Sep 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10417-10421
Article type
Edge Article

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, 10, 10417
DOI: 10.1039/C9SC04177J

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    [Original citation] - Published by The Royal Society of Chemistry.

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