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Redox‐Neutral α‐Allylation of Amines by Combining Palladium Catalysis and Visible‐Light Photoredox Catalysis
Authors:Jun Xuan  Ting‐Ting Zeng  Zhu‐Jia Feng  Qiao‐Hui Deng  Prof. Dr. Jia‐Rong Chen  Dr. Liang‐Qiu Lu  Prof. Dr. Wen‐Jing Xiao  Prof. Dr. Howard Alper
Affiliation:1. CCNU‐uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem‐xiao.ccnu.edu.cn/;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China);3. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000 (China);4. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada)
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.
Keywords:allylic compounds  palladium  photochemistry  radicals  synthetic methods
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