Issue 44, 2019

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 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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2019,10, 10417-10421

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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