Redox-Neutral [alpha]-Allylation of Amines by Combining Palladium Catalysis and Visible-Light Photoredox Catalysis

An unprecedented [alpha]-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 red...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-01, Vol.54 (5), p.1625
Main Authors: Xuan, Jun, Zeng, Ting-Ting, Feng, Zhu-Jia, Deng, Qiao-Hui, Chen, Jia-Rong, Lu, Liang-Qiu, Xiao, Wen-Jing, Alper, Howard
Format: Article
Language:English
Subjects:
Catalysis
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Summary:An unprecedented [alpha]-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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409999