Palladium catalyzed selective arylation of B(4)-H of o-carboranes with potassium aryltrifluoroborate

被引:1
|
作者
Teng, Chao-Chao [1 ,2 ]
Guo, Yan [3 ]
Cao, Ke [1 ,2 ,3 ]
Yang, Han-Bo [1 ,2 ]
Jiang, Qi-Jia [1 ,2 ]
Zhu, Dao-Yong [4 ,5 ]
Wang, Shao-Hua [4 ,5 ]
机构
[1] Southwest Univ Sci & Technol, State Key Lab Environm Friendly Energy Mat, 59 Qinglong Rd, Mianyang 621010, Sichuan, Peoples R China
[2] Southwest Univ Sci & Technol, Sch Mat & Chem, 59 Qinglong Rd, Mianyang 621010, Sichuan, Peoples R China
[3] Sichuan Sci City Hosp, Dept Oncol, Mianyang 621000, Sichuan, Peoples R China
[4] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China
[5] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
Carborane; B -H activation; Selective arylation; Potassium phenyltrifluoroborate; B-H ACTIVATION; AMIDATION; EMISSION; BONDS;
D O I
10.1016/j.jorganchem.2024.123051
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A palladium catalyzed selective arylation of B(4) -H of 9-amide-o-carborane with potassium aryltrifluoroborate has been developed. A series of B(4)-Ar-B(9)-amide-o-carborane derivatives decorated with diverse active groups have been synthesized with moderate to good yields as well as excellent selectivity. This work represents an unprecedented protocol for selective arylation of o-carboranes with potassium aryltrifluoroborates.
引用
收藏
页数:7
相关论文
共 50 条
  • [31] Palladium-Catalyzed Selective Mono-/Tetraacetoxylation of o-Carboranes with Acetic Acid via Cross Dehydrogenative Coupling of Cage B-H/O-H Bonds
    Xu, Tao-Tao
    Cao, Ke
    Wu, Ji
    Zhang, Cai-Yan
    Yang, Junxiao
    INORGANIC CHEMISTRY, 2018, 57 (05) : 2925 - 2932
  • [32] Palladium-Catalyzed Regioselective B(9)-Amination of o-Carboranes and m-Carboranes in HFIP with Broad Nitrogen Sources
    Ma, Yan-Na
    Gao, Yan
    Ma, Yubin
    Wang, Yan
    Ren, Huazhan
    Chen, Xuenian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (18) : 8371 - 8378
  • [33] Regiodivergent metal-catalyzed B(4)- and C(1)-selenylation of o-carboranes
    Lee, Kyungsup
    Harper, Jordan L.
    Kim, Tae Hyeon
    Noh, Hee Chan
    Kim, Dongwook
    Cheong, Paul Ha-Yeon
    Lee, Phil Ho
    CHEMICAL SCIENCE, 2023, 14 (03) : 643 - 649
  • [34] Palladium Catalyzed Regioselective B-C(sp) Coupling via Direct Cage B-H Activation: Synthesis of B(4)-Alkynylated o-Carboranes
    Quan, Yangjian
    Tang, Cen
    Xie, Zuowei
    SYNTHESIS-STUTTGART, 2016, 48 (23): : A177 - A179
  • [35] Catalytic Regioselective Cage B(8)-H Arylation of o-Carboranes via "Cage-Walking" Strategy
    Lyu, Hairong
    Zhang, Jie
    Yang, Jingting
    Quan, Yangjian
    Xie, Zuowei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (10) : 4219 - 4224
  • [36] Rhodium(III)-Catalyzed B(4)-Azo Coupling of o-Carboranes with Aryl Diazonium Tetrafluoroborates
    Lee, Kyungsup
    Yoon, Sugyeong
    Noh, Hee Chan
    Kim, Dongwook
    Lee, Phil Ho
    ORGANIC LETTERS, 2024, 26 (39) : 8410 - 8415
  • [37] 8-Aminoquinoline as a bidentate traceless directing group for Cu-catalyzed selective B(4,5)-H disulfenylation of o-carboranes
    Chen, Yu
    Quan, Yangjian
    Xie, Zuowei
    CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 12997 - 13000
  • [38] Old Key Opens the Lock in Carborane: The in Situ NHC-Palladium Catalytic System for Selective Arylation of B(3,6)-H Bonds of o-Carboranes via B-H Activation
    Xu, Tao-Tao
    Cao, Ke
    Zhang, Cai-Yan
    Wu, Ji
    Ding, Li-Fang
    Yang, Junxiao
    ORGANIC LETTERS, 2019, 21 (22) : 9276 - 9279
  • [39] Selective Labeling of Peptides with o-Carboranes via Manganese(I)-Catalyzed C-H Activation
    Jei, Becky Bongsuiru
    Yang, Long
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (37)
  • [40] Transition Metal Catalyzed, Regioselective B(4)-Halogenation and B(4,5)-Diiodination of Cage B-H Bonds in o-Carboranes
    Lyu, Hairong
    Quan, Yangjian
    Xie, Zuowei
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (59) : 14866 - 14871