Directing-Group-Assisted Transition-Metal-Catalyzed Selective BH Functionalization of o-Carboranes

被引:3
作者
Zhang, Jie [1 ,2 ]
Xie, Zuowei [3 ,4 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China
[3] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[4] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
来源
SYNTHESIS-STUTTGART | 2025年 / 57卷 / 03期
基金
中国国家自然科学基金;
关键词
BH functionalization; directing groups; transition metals; catalysis; o; -carboranes; H ACTIVATION; STRUCTURAL-CHARACTERIZATION; BORON CLUSTERS; HALIDE FREE; BONDS; DERIVATIVES; ARYLATION; FACILE; CARBON; 1,2-DICARBACLOVODODECABORANE(12);
D O I
10.1055/a-2343-0780
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboranes are a type of molecular clusters consisting of carbon, hydrogen, and boron atoms. They possess unique characteristics, such as three-dimensional aromaticity, icosahedral geometry, and robustness. Functionalized carboranes have been utilized in various fields, including medicine, materials, and organometallic/coordination chemistry. In this context, selective functionalization of o -carboranes has received tremendous attention, specifically in the regio- and enantioselective modification of the ten chemically similar BH vertices within the carborane cage. In recent years, significant progress has been made in catalytic vertex-specific BH functionalization, as well as achieving enantioselective functionalization of the cage BH. This review provides an overview of the recent advancements in this research field.
引用
收藏
页码:495 / 521
页数:27
相关论文
共 129 条
  • [1] Recent Advances in Transition Metal-Catalyzed Selective B-H Functionalization of o-Carboranes
    Au, Yik Ki
    Xie, Zuowei
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (03) : 879 - 899
  • [2] Palladium-Catalyzed Carbonylative Annulation of 1-Hydroxy-o-Carborane and Internal Alkynes via Regioselective B-H Activation
    Au, Yik Ki
    Quan, Yangjian
    Xie, Zuowei
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (14) : 2170 - 2173
  • [3] Copper-Catalyzed Electrochemical Selective B-H Oxygenation of o-Carboranes at Room Temperature
    Au, Yik Ki
    Lyu, Hairong
    Quan, Yangjian
    Xie, Zuowei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (15) : 6940 - 6945
  • [4] One-Pot Process to Carborano-Coumarin via Catalytic CascadeDehydrogenative Cross-Coupling
    Au, Yik Ki
    Lyu, Hairong
    Quan, Yangjian
    Xie, Zuowei
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (04) : 383 - 388
  • [5] Catalytic Cascade Dehydrogenative Cross-Coupling of BH/CH and BH/NH: One-Pot Process to Carborano-Isoquinolinone
    Au, Yik Ki
    Lyu, Hairong
    Quan, Yangjian
    Xie, Zuowei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (32) : 12855 - 12862
  • [6] Iridium-Catalyzed Cyclative Indenylation and Dienylation through Sequential B(4)-C Bond Formation, Cyclization, and Elimination from o-Carboranes and Propargyl Alcohols
    Baek, Yonghyeon
    Cheong, Kiun
    Ko, Gi Hoon
    Han, Gi Uk
    Han, Sang Hoon
    Kim, Dongwook
    Lee, Kooyeon
    Lee, Phil Ho
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (22) : 9890 - 9895
  • [7] Rhodium-Catalyzed Amidation of the Cage B(4)-H Bond in o-Carboranes with Dioxazolones by Carboxylic Acid-Assisted B(4)-H Bond Activation
    Baek, Yonghyeon
    Kim, Suhui
    Son, Jeong-Yu
    Lee, Kooyeon
    Kim, Dongwook
    Lee, Phil Ho
    [J]. ACS CATALYSIS, 2019, 9 (11) : 10418 - 10425
  • [8] The synthesis of carboracycles derived from B,B′-Bis(aryl) derivatives of icosahedral ortho-carborane
    Bayer, MJ
    Herzog, A
    Diaz, M
    Harakas, GA
    Lee, H
    Knobler, CB
    Hawthorne, MF
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (12) : 2732 - 2744
  • [9] Palladium-catalyzed amination of 2-iodo-para-carborane
    Beletskaya, Irina P.
    Bregadze, Vladimir I.
    Kabytaev, Kuanysh Z.
    Zhigareva, Galina G.
    Petrovskii, Pavel V.
    Glukhov, Ivan V.
    Starikova, Zoya A.
    [J]. ORGANOMETALLICS, 2007, 26 (09) : 2340 - 2347
  • [10] Acid-Induced Opening of [closo-B10H10]2- as a New Route to 6-Substituted nido-B10H13 Decaboranes and Related Carboranes
    Bondarev, Oleg
    Sevryugina, Yulia V.
    Jalisatgi, Satish S.
    Hawthorne, M. Frederick
    [J]. INORGANIC CHEMISTRY, 2012, 51 (18) : 9935 - 9942