Catalyst-free benzylic C(sp3)-H cross-coupling with organotrifluoroborates enabled by electrochemistry

被引:14
|
作者
Li, Chao [1 ]
Ding, Ran [1 ,3 ]
Guo, Heng-Yi [2 ]
Xia, Shuang [2 ]
Shu, Lei [1 ]
Wang, Pei-Long [1 ,2 ]
Li, Hongji [1 ]
机构
[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ, Huaibei 235000, Anhui, Peoples R China
[2] Huaibei Normal Univ, Informat Coll, Huaibei 235000, Peoples R China
[3] Anhui Sci & Technol Univ, Coll Chem & Mat Engn, Bengbu 233100, Anhui, Peoples R China
基金
美国国家科学基金会;
关键词
C-H BONDS; AMINATION; FUNCTIONALIZATION; ALKYLATION; ACTIVATION; XANTHENES; OXIDATION; ETHERS; SALTS; ACIDS;
D O I
10.1039/d2gc02204d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a rare catalyst-free electrochemical cross-coupling of benzylic C-H bonds with organotrifluoroborates, which readily proceeds at room temperature and provides a unique protocol for forging C(sp(3))-C(sp(3)), C(sp(3))-C(sp(2)) and C(sp(3))-C(sp) bonds. In particular, this work discloses the dual role of organotrifluoroborates serving both as a coupling partner and an electrolyte in C(sp(3))-H functionalization.
引用
收藏
页码:7883 / 7888
页数:6
相关论文
共 50 条
  • [21] Electrochemical oxidative C(sp3)-H cross-coupling with hydrogen evolution
    Yang, Zhaoliang
    Shi, Wenyan
    Alhumade, Hesham
    Yi, Hong
    Lei, Aiwen
    NATURE SYNTHESIS, 2023, 2 (03): : 217 - 230
  • [22] Direct C(sp3)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals
    Shields, Benjamin J.
    Doyle, Abigail G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) : 12719 - 12722
  • [23] Electro-oxidative C(sp3)-H Amination of Azoles via Intermolecular Oxidative C(sp3)-H/N-H Cross-Coupling
    Wu, Jiwei
    Zhou, Yi
    Zhou, Yuchen
    Chiang, Chien-Wei
    Lei, Aiwen
    ACS CATALYSIS, 2017, 7 (12): : 8320 - 8323
  • [24] Cross-Coupling Reactions between C(sp2)-H and C(sp3)-H Bonds via Sequential Dehydrogenation and C-H Insertion
    Kuninobu, Yoichiro
    Asanoma, Daisuke
    Takai, Kazuhiko
    SYNLETT, 2010, (19) : 2883 - 2886
  • [25] Electrochemical α-C(sp3)-H/O-H cross-coupling of isochromans and alcohols assisted by benzoic acid
    Wang, Zhuang
    Niu, Kaikai
    Liu, Yuxiu
    Song, Hongjian
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2022, 58 (78) : 10949 - 10952
  • [26] Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions
    Jiang, Chao
    Chen, Pinhong
    Liu, Guosheng
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (10) : 2858 - 2862
  • [27] Photoredox/Nickel Dual Catalysis for the C(sp3)-C(sp3) Cross-Coupling of Alkylsilicates with Alkyl Halides
    Leveque, Christophe
    Corce, Vincent
    Chenneberg, Ludwig
    Ollivier, Cyril
    Fensterbank, Louis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2118 - 2121
  • [28] Catalyst-free direct C(sp3)-H sulfenylation of xanthene derivatives using air as the oxidant
    Chen, Qian
    Yu, Guodian
    Wang, Xiaofeng
    Ou, Yingcong
    Huo, Yanping
    GREEN CHEMISTRY, 2019, 21 (04) : 798 - 802
  • [29] Catalyst-free photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines
    Zhou, Jingwei
    Wang, Songping
    Duan, Wentao
    Lian, Qi
    Wei, Wentao
    GREEN CHEMISTRY, 2021, 23 (09) : 3261 - 3267
  • [30] Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp3)-H and C(sp2)-H Bonds
    Wu, Zhuo
    Wu, Zechen
    Sun, Xueliang
    Qi, Weixin
    Zhang, Zhengyang
    Zhang, Yanghui
    ORGANIC LETTERS, 2021, 23 (18) : 7161 - 7165