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Regioselective and Stereospecific Cross-Coupling of Primary Allylic Amines with Boronic Acids and Boronates through Palladium-Catalyzed C[BOND]N Bond Cleavage

Authors

  • Man-Bo Li,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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  • Yong Wang,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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  • Prof. Dr. Shi-Kai Tian

    Corresponding author
    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
    2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
    • Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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  • We are grateful for the financial support from the National Natural Science Foundation of China (21172206 and 20972147), the National Basic Research Program of China (973 Program 2010CB833300), and the Program for Changjiang Scholars and Innovative Research Team in University (IRT1189).

Abstract

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Die NH2-Gruppe fungiert in der palladiumkatalysierten regioselektiven und stereospezifischen Titelreaktion als effektive Abgangsgruppe (siehe Schema). Die Reaktion gelingt mit Aryl- und Alkenylboronsäuren sowie Aryl-, Alkenyl-, Allyl- und Benzylboronaten. Mit α-chiralen primären Allylaminen als allylischen Elektrophilen wurde ein vollständiger Chiralitätstransfer erreicht.

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