Copper-catalyzed benzylic oxidation of C(sp3)-H bonds

被引:22
|
作者
Zhang, Bo
Zhu, Shou-Fei [1 ]
Zhou, Qi-Lin
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper catalyst; Quinoline-imine ligand; Benzylic oxidation; C(sp(3))-H bond functionalization; C-H BONDS; ENANTIOSELECTIVE ALLYLIC OXIDATION; 2-ARYLACETIC ACID-DERIVATIVES; ALPHA-HYDROXYLATION; COMPLEX; FUNCTIONALIZATION; ACTIVATION; EFFICIENT;
D O I
10.1016/j.tet.2012.12.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A selective oxidation of benzylic C(sp(3))-H bonds to C(sp(3))-O bonds catalyzed by copper complexes of quinoline-imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C-H bond functionalization. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2033 / 2037
页数:5
相关论文
共 50 条
  • [1] Copper-catalyzed benzylic C(sp3)-H alkoxylation of heterocyclic compounds
    Takemura, Noriaki
    Kuninobu, Yoichiro
    Kanai, Motomu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (16) : 2528 - 2532
  • [2] Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones
    Nozawa-Kumada, Kanako
    Matsuzawa, Yuta
    Ono, Kanako
    Shigeno, Masanori
    Kondo, Yoshinori
    CHEMICAL COMMUNICATIONS, 2021, 57 (69) : 8604 - 8607
  • [3] Copper-catalyzed oxidative benzylic C(sp3)-H amination: direct synthesis of benzylic carbamates
    Liu, Shuai
    Achou, Raphael
    Boulanger, Coline
    Pawar, Govind
    Kumar, Nivesh
    Lusseau, Jonathan
    Robert, Frederic
    Landais, Yannick
    CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 13013 - 13016
  • [4] Copper-Catalyzed Late-Stage Benzylic C(sp3)-H Trifluoromethylation
    Xiao, Haiwen
    Liu, Zhonglin
    Shen, Haigen
    Zhang, Benxiang
    Zhu, Lin
    Li, Chaozhong
    CHEM, 2019, 5 (04): : 940 - 949
  • [5] Copper-Catalyzed Oxidative Benzylic C(sp3)-H Cyclization for the Synthesis of β-Lactams
    Nozawa-Kumada, Kanako
    Saga, Satoshi
    Matsuzawa, Yuta
    Hayashi, Masahito
    Shigeno, Masanori
    Kondo, Yoshinori
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (20) : 4496 - 4499
  • [6] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [7] Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation
    Chen, Chao
    Xu, Xiu-Hua
    Yang, Bin
    Qing, Feng-Ling
    ORGANIC LETTERS, 2014, 16 (12) : 3372 - 3375
  • [8] Copper-Catalyzed Aerobic Benzylic C(sp3)-H Oxidation of Unprotected Aniline Derivatives for the Synthesis of Phenanthridines
    Nozawa-Kumada, Kanako
    Matsuzawa, Yuta
    Hayashi, Masahito
    Kobayashi, Takumi
    Shigeno, Masanori
    Yada, Akira
    Kondo, Yoshinori
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2241 - 2245
  • [9] Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Yu, Fan
    Wang, Wengui
    Wang, Shoufeng
    ORGANIC LETTERS, 2024, 26 (10) : 2068 - 2072
  • [10] Mechanism and Selectivity of Copper-Catalyzed Bromination of Distal C(sp3)-H Bonds
    Ajitha, Manjaly J.
    Haines, Brandon E.
    Musaev, Djamaladdin G.
    ORGANOMETALLICS, 2023, 42 (18) : 2467 - 2476