Get access

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)
    Search for more papers by this author
  • Yong Wang,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
    Search for more papers by this author
  • 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)
    Search for more papers by this author

  • 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

original image

The NH2 group serves as an effective leaving group in the palladium-catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl- and alkenylboronic acids and aryl-, alkenyl-, allyl-, and benzylboronates, and complete transfer of chirality has been achieved when using α-chiral primary allylic amines as the allylic electrophiles.

Get access to the full text of this article

Ancillary