Regioselective Nucleophilic Alkylation/Arylation of B-H Bonds in o-Carboranes: An Alternative Method for Selective Cage Boron Functionalization

被引：41
|
作者：
Tang, Cen
Zhang, Jiji
Zhang, Jie
Xie, Zuowei [1 ]
机构：
[1] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 48期
关键词：
FACILE SYNTHESIS; ARYL IODIDES; ACTIVATION; AROMATICITY; ARYLATION; LIGAND; METALLACARBORANES; ALKENYLATION; COMPLEXES; CLUSTERS;
D O I：
10.1021/jacs.8b10270
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new protocol for regioselective nucleophilic cage B-H substitution in o-carboranes has been proposed that is complementary to the strategies of transition metal catalysis and electrophilic substitution. Magnesium-mediated site-selective nucleophilic cage B-(3,6)-H and B(9)-H substitution reactions of o-carboranes give a series of B(3,6)-dialkylated and B(9)-alkylated/arylated o-carboranes in high yields. Both steric and electronic factors of cage C substituents play crucial roles in controlling the site selectivity.
引用
收藏
页码：16423 / 16427
页数：5
相关论文
共 50 条
  • [21] 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
  • [22] Ir-catalyzed enantioselective B-H alkenylation for asymmetric synthesis of chiral-at-cage o-carboranes
    Cheng, Ruofei
    Zhang, Jie
    Zhang, Huifang
    Qiu, Zaozao
    Xie, Zuowei
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [23] 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
  • [24] Iridium-Induced Regioselective B-H and C-C Activations at Azo-Substituted o-Carboranes
    Gao, Yang
    Cui, Peng-Fei
    Aznarez, Francisco
    Jin, Guo-Xin
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (41) : 10357 - 10363
  • [25] Enantioselective Synthesis of Chiral-at-Cage o-Carboranes via Pd-Catalyzed Asymmetric B-H Substitution
    Cheng, Ruofei
    Li, Bowen
    Wu, Jie
    Zhang, Jie
    Qiu, Zaozao
    Tang, Wenjun
    You, Shu-Li
    Tang, Yong
    Xie, Zuowei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (13) : 4508 - 4511
  • [26] Iridium-Catalyzed Regioselective B(3)-Alkenylation/B(3,6)-Dialkenylation of o-Carboranes by Direct B-H Activation
    Cheng, Ruofei
    Qiu, Zaozao
    Xie, Zuowei
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (32) : 7212 - 7218
  • [27] Palladium-catalyzed selective B(3)-H arylation of o-carboranes with arylboronic acids at room temperature
    Yang, Ziyi
    Wu, Yuanbo
    Fu, Yatong
    Yang, Jianxin
    Lu, Jian
    Lu, Ju-You
    CHEMICAL COMMUNICATIONS, 2021, 57 (13) : 1655 - 1658
  • [28] A variable bidentate traceless directing group for nickel-catalyzed regioselective B-H poly-chalcogenation of o-carboranes
    Li, Ping
    Qiu, Zihuan
    Lu, Jian
    Lu, Ju-You
    INORGANIC CHEMISTRY FRONTIERS, 2025, 12 (05): : 1994 - 2002
  • [29] Iridium-Catalyzed Cage B(4)-Amidation Reaction of o-Carboranes with Dioxazolones: Selective Synthesis of Amidated o-Carboranes and Amidated and Methoxycarbonylated nido-Carboranes
    Han, Gi Uk
    Baek, Yonghyeon
    Lee, Kyungsup
    Shin, Seohyun
    Noh, Hee Chan
    Lee, Phil Ho
    ORGANIC LETTERS, 2021, 23 (02) : 416 - 420
  • [30] Iridium(III)-Catalyzed Regioselective B(4)-H Amination of o-Carboranes with Sufilimines
    Park, Kyeongna
    Han, Gi Uk
    Yoon, Sugyeong
    Lee, Eunseo
    Noh, Hee Chan
    Lee, Kyungsup
    Maeng, Chanyoung
    Kim, Dongwook
    Lee, Phil Ho
    ORGANIC LETTERS, 2023, 25 (32) : 5989 - 5994
12345