Redox‐Neutral α‐Allylation of Amines by Combining Palladium Catalysis and Visible‐Light Photoredox Catalysis

Jun Xuan, Tingting Zeng, Zhu‐Jia Feng, Qiao‐Hui Deng, Jia‐Rong Chen, Liang‐Qiu Lu, Wen‐Jing Xiao, Howard Alper

Angewandte Chemie International Edition · 2014 · 278 citations · 41 references

Concepts

Abstract

An unprecedented α-allylation of amines was achieved by combining palladium catalysis and visible-light photoredox catalysis. In this dual catalysis process, the catalytic generation of allyl radical from the corresponding π-allylpalladium intermediate was achieved without additional metal reducing reagents (redox-neutral). Various allylation products of amines were obtained in high yields through radical cross-coupling under mild reaction conditions. Moreover, the transformation was applied to the formal synthesis of 8-oxoprotoberberine derivatives which show potential anticancer properties.

References

41