Selective, radical-free activation of benzylic C-H bonds in methylarenes

被引:3
|
作者
Chan, Antony P. Y. [1 ]
Jakoobi, Martin [1 ]
Wang, Chenxu [1 ]
Tian, Yancong [1 ]
Halcovitch, Nathan [2 ]
Boulatov, Roman [1 ]
Sergeev, Alexey G. [1 ]
机构
[1] Univ Liverpool, Dept Chem, Crown St, Liverpool L69 7ZD, Merseyside, England
[2] Univ Lancaster, Dept Chem, Lancaster LA1 4YW, England
基金
美国国家科学基金会; 英国工程与自然科学研究理事会;
关键词
CATALYZED BORYLATION; FUNCTIONALIZATION; MECHANISM; HYDROCARBONS; PHOTOLYSIS; IRIDIUM; ARENES;
D O I
10.1039/d1cc03445f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report rare examples of exclusive benzylic C-H oxidative addition in industrially important methylarenes using simple eta(4)-arene iridium complexes. Mechanistic studies showed that coordinatively unsaturated eta(2)-arene intermediates are responsible for the selective activation of benzylic, not aromatic C-H bonds and formation of stable benzyl complexes after trapping with a phosphine ligand.
引用
收藏
页码:7894 / 7897
页数:4
相关论文
共 50 条
  • [31] Copper-catalyzed enantioselective cyanation of benzylic C-H bonds via radical relay
    Liang, Yujie
    Jiao, Ning
    SCIENCE CHINA-CHEMISTRY, 2017, 60 (01) : 105 - 106
  • [32] Selective Oxidation of Benzylic C-H Bonds Catalyzed by Cu(II)/{PMo12}
    Li, Peihe
    Wang, Yingying
    Wang, Xia
    Wang, Yin
    Liu, Ying
    Huang, Keke
    Hu, Jing
    Duan, Limei
    Hu, Changwen
    Liu, Jinghai
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3101 - 3109
  • [33] Late-Stage Trifluoromethylthiolation of Benzylic C-H Bonds
    Xie, Jin
    Zhu, Chengjian
    Xu, Wentao
    Wang, Wenliang
    Liu, Tao
    SYNTHESIS-STUTTGART, 2020, 52 (03): : A28 - A29
  • [34] Selective functionalization of C-H bonds
    Hartwig, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [35] Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds
    Jung, Hoimin
    Schrader, Malte
    Kim, Dongwook
    Baik, Mu-Hyun
    Park, Yoonsu
    Chang, Sukbok
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (38) : 15356 - 15366
  • [36] Late-stage trifluoromethylthiolation of benzylic C-H bonds
    Xu, Wentao
    Wang, Wenliang
    Liu, Tao
    Xie, Jin
    Zhu, Chengjian
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [37] Silver-Catalyzed Oxidative Activation of Benzylic C-H Bonds for the Synthesis of Difluoromethylated Arenes
    Xu, Peng
    Guo, Shuo
    Wang, Liyan
    Tang, Pingping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) : 5955 - 5958
  • [38] Late-stage trifluoromethylthiolation of benzylic C-H bonds
    Wentao Xu
    Wenliang Wang
    Tao Liu
    Jin Xie
    Chengjian Zhu
    Nature Communications, 10
  • [39] A photochromic composite with enhanced carrier separation for the photocatalytic activation of benzylic C-H bonds in toluene
    Cao, Xing
    Chen, Zheng
    Lin, Rui
    Cheong, Weng-Chon
    Liu, Shoujie
    Zhang, Jian
    Peng, Qing
    Chen, Chen
    Han, Tong
    Tong, Xuanjue
    Wang, Yu
    Shen, Rongan
    Zhu, Wei
    Wang, Dingsheng
    Li, Yadong
    NATURE CATALYSIS, 2018, 1 (09): : 704 - 710
  • [40] ACTIVATION OF C-H BONDS IN TETRAHYDROFURAN
    NEKHAEV, AI
    KOLOBKOV, BI
    ALEKSANDROV, GG
    TASHEV, MT
    DUSTOV, KB
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1987, 36 (03): : 638 - 638