Organic Chemistry

Nickel-Catalyzed Hydroalkylation and Hydroalkenylation of 1,3-Dienes with Hydrazones

Abstract

In this article, we report a protocol for nickel catalyzed hydroalkylation of dienes with hydrazones, which serve as equivalents of unstabilized 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.

Content

Thumbnail image of cl-hydroalkylation-190610-chemRxiv.pdf

Supplementary material

Thumbnail image of cl-hydroalkylation-SI-190610-chemRxiv.pdf
cl-hydroalkylation-SI-190610-chemRxiv