Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1568-1575.DOI: 10.6023/cjoc202310018 Previous Articles     Next Articles

ARTICLES

钯催化邻-碳硼烷基吡啶卤化物交叉偶联合成邻-碳硼烷基联芳、氨基吡啶和炔基吡啶衍生物

罗东红a,†, 李平a,†, 陈志才b,†, 杨佳怡a, 孙梦凡a, 陆居有a,*()   

  1. a 海南大学化学化工学院 海口 570228
    b 海南大学材料科学与工程学院 南海海洋资源利用国家重点实验室 海口 570228
  • 收稿日期:2023-10-21 修回日期:2024-01-13 发布日期:2024-01-30
  • 作者简介:
    †共同第一作者
  • 基金资助:
    国家自然科学基金(22161015); 海南省自然科学基金(221RC448)

Pd-Catalyzed Cross-Coupling of o-Carboranyl Pyridyl Halides: Synthesis of o-Carboranyl Biaryls, Aminopyridines and Alkynylpyridine Derivatives

Donghong Luoa,†, Ping Lia,†, Zhicai Chenb,†, Jiayi Yanga, Mengfan Suna, Juyou Lua()   

  1. a School of Chemistry and Chemical Engineering, Hainan University, Haikou 570228
    b State Key Laboratory of Marine Resource Utilization in South China Sea, College of Materials Science and Engineering, Hainan University, Haikou 570228
  • Received:2023-10-21 Revised:2024-01-13 Published:2024-01-30
  • Contact: *E-mail: lujy@hainanu.edu.cn
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22161015); Hainan Provincial Natural Science Foundation of China(221RC448)

The Suzuki cross-coupling reaction between readily available o-carboranyl-substituted pyridyl halides and (hete- ro)arylboronic acids under Pd catalysis has been developed, providing access to o-carboranyl biaryls in yields of 35%~92%. The transformations proceed under mild conditions and with high functional group tolerance using commercially available coupling partners. Furthermore, the Buchwald-Hartwig reaction and Sonogashira reaction of o-carboranyl pyridyl halides are reported as well, leading to the facile synthesis of o-carboranyl aminopyridines and alkynylpyridine derivatives, respectively. It is believed that these heteroarylated carborane derivatives may find applications in luminescent materials and drug discovery.

Key words: carborane, carboranyl pyridyl halides, cross coupling, palladium catalysis