Mutual Activation: Suzuki–Miyaura Coupling through Direct Cleavage of the sp2 C[BOND]O Bond of Naphtholate

Authors

  • Da-Gang Yu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890
    Search for more papers by this author
  • Prof. Zhang-Jie Shi

    Corresponding author
    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China) http://pku.edu.cn/zshi/
    • Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890
    Search for more papers by this author

  • We thank Prof. Wen-Xiong Zhang, Dr. Neng-Dong Wang, Prof. Xiang Hao, and Shao-Guang Zhang for the X-ray crystallographic analysis, and Prof. Zhi-Xiang Yu and Qian Li for the use of their glove box. D.-G. Yu thanks Bi-Jie Li, Bing-Tao Guan, Yang Li, and Chang-Liang Sun for constructive discussion, and Xiao-Bo Zhang and Xin Wang for their help in preparation of some of the compounds. Support of this work by NSFC (No. 20925207, 21072010, 20821062) and the “973” Project from the MOST of China (2009CB825300) is gratefully acknowledged.

Abstract

original image

Teamarbeit kennzeichnet den neuen Ansatz der wechselseitigen Aktivierung von Naphtholaten und Arylboronsäurederivaten: Die Bildung von Boraten erleichtert die Suzuki-Miyaura-Kupplung durch direkte nickelkatalysierte Spaltung der sp2-C-O-Bindung (siehe Schema; R′: anelliertes Ringsystem). Eine Reihe von Naphtholaten und Arylboronsäurederivaten konnte mit guten Ausbeuten direkt gekuppelt werden.

Ancillary