Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3078-3085.DOI: 10.6023/cjoc201805018 Previous Articles     Next Articles

Special Issue: 碳氢活化合辑2018-2019



许新彬a,b, 程若飞b, 邱早早b, 潘成岭a   

  1. a 安徽理工大学化学工程学院 多尺度材料与分子催化实验室 淮南 232001;
    b 中国科学院上海有机化学研究所 沪港化学合成联合实验室 上海 200032
  • 收稿日期:2018-05-07 修回日期:2018-06-20 发布日期:2018-07-05
  • 通讯作者: 邱早早, 潘成岭;
  • 基金资助:


Palladium-Catalyzed Cross-Coupling Reactions of Borylated o-Carborane: Synthesis of 3,6-Diaryl-o-carboranes

Xu Xinbina,b, Cheng Ruofeib, Qiu Zaozaob, Pan Chenglinga   

  1. a Laboratory of Multiscale Materials and Molecular Catalysis, School of Materials Science and Engineering, Anhui University of Science and Technology, Huainan 232001;
    b Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-05-07 Revised:2018-06-20 Published:2018-07-05
  • Supported by:

    Project supported by the the National Natural Science Foundation of China (No. 21772223) and the CAS-Croucher Funding Scheme.

Palladium catalyzed cross-coupling of 3,6-(Bpin)2-o-carborane (Bpin=pinacolatoboryl) with aryl bromides has been achieved, leading to the formation of a series of B(3,6)-diarylated-o-carborane derivatives in moderate yields. In this reaction, PdCl2(cod)/tricyclohexylphosphine was used as catalyst to avoid the formation of palladium-catalyzed aryl-aryl exchange and direct B-H arylation by-products. A possible mechanism is proposed, involving a tandem sequence of oxidative addition, anion exchange, transmetalation, and reductive elimination.

Key words: carborane, coupling reaction, palladium, carboranyl boronate, aryl bromide