Photocatalytic Generation of N‐Centered Hydrazonyl Radicals:  A Strategy for Hydroamination of β,γ‐Unsaturated Hydrazones

Xiao‐Qiang Hu, Jia‐Rong Chen, Qiang Wei, Feng‐Lei Liu, Qiao‐Hui Deng, André M. Beauchemin, Wen‐Jing Xiao

Angewandte Chemie International Edition · 2014 · 298 citations · 55 references

Concepts

Abstract

A visible-light photocatalytic generation of N-centered hydrazonyl radicals has been accomplished for the first time. This approach allows efficient intramolecular addition of hydrazonyl radical to terminal alkenes, thus providing hydroamination and oxyamination products in good yields. Importantly, the protocol involves deprotonation of an N-H bond and photocatalytic oxidation to an N-centered radical, thus obviating the need to prepare photolabile amine precursors or the stoichiometric use of oxidizing reagents.

References

55