Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant C═C Bond Cleavage

Org Lett. 2020 Oct 16;22(20):7981-7985. doi: 10.1021/acs.orglett.0c02911. Epub 2020 Oct 6.

Abstract

A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant C═C bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.