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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†

  1. Man-Bo Li1,
  2. Yong Wang1,
  3. Prof. Dr. Shi-Kai Tian1,2,*

Article first published online: 14 FEB 2012

DOI: 10.1002/anie.201109171

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 12, pages 2968–2971, March 19, 2012

Additional Information

How to Cite

Li, M.-B., Wang, Y. and Tian, S.-K. (2012), Regioselective and Stereospecific Cross-Coupling of Primary Allylic Amines with Boronic Acids and Boronates through Palladium-Catalyzed C[BOND]N Bond Cleavage . Angew. Chem. Int. Ed., 51: 2968–2971. doi: 10.1002/anie.201109171

Author Information

  1. 1

    Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)

  2. 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)

  1. †

    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).

Publication History

  1. Issue published online: 13 MAR 2012
  2. Article first published online: 14 FEB 2012
  3. Manuscript Received: 27 DEC 2011

Funded by

  • National Natural Science Foundation of China. Grant Numbers: 21172206, 20972147
  • National Basic Research Program of China. Grant Number: 2010CB833300
  • Program for Changjiang Scholars and Innovative Research Team in University. Grant Number: IRT1189

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Keywords:

  • allylic compounds;
  • C[BOND]N bond cleavage;
  • cross-coupling;
  • boron;
  • palladium
Thumbnail image of graphical abstract

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.

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