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
来源：
GREEN CHEMISTRY | 2022年 / 24卷 / 20期
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
  • [1] Ligand-Enabled Cross-Coupling of C(sp3)-H Bonds with Arylsilanes
    He, Jian
    Takise, Ryosuke
    Fu, Haiyan
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (14) : 4618 - 4621
  • [2] Benzylic C(sp3)-C(sp2) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis
    Kim, Weonjeong
    Koo, Jangwoo
    Lee, Hong Geun
    CHEMICAL SCIENCE, 2021, 12 (11) : 4119 - 4125
  • [3] Catalyst-free benzylic C(sp3)-H functionalization of methyl quinolines with tryptanthrins
    Zheng, Zhu
    Wu, Quanquan
    Liu, Chong-Xing
    Yang, Zhannan
    Liu, Hongxin
    SYNTHETIC COMMUNICATIONS, 2018, 48 (09) : 1092 - 1098
  • [4] Copper-catalyzed radical oxidative C(sp3)-H/C(sp3)-H cross-coupling between arylacetonitriles and benzylic compounds
    Xiao, Jing
    Li, Fangshao
    Zhong, Ting
    Wu, Xiaofang
    Guo, Fengzhe
    Li, Qiang
    Tang, Zi-Long
    TETRAHEDRON, 2020, 76 (48)
  • [5] Metal-free photoinduced C(sp3)-H/C(sp3)-H cross-coupling to access α-tertiary amino acid derivatives
    Li, Yujun
    Guo, Shaopeng
    Li, Qing-Han
    Zheng, Ke
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [6] Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2)-H/C(sp3)-H Cross-Coupling
    Wen, Jiangwei
    Zhang, Fan
    Shi, Wenyan
    Lei, Aiwen
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (37) : 8814 - 8817
  • [7] Decarboxylative C(sp3)-O Cross-Coupling
    Mao, Runze
    Balon, Jonathan
    Hu, Xile
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (41) : 13624 - 13628
  • [8] Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(o) catalysis
    Chan, Kelvin S. L.
    Wasa, Masayuki
    Chu, Ling
    Laforteza, Brian N.
    Miura, Masanori
    Yu, Jin-Quan
    NATURE CHEMISTRY, 2014, 6 (02) : 146 - 150
  • [9] Selectively Oxidative C(sp2)-H/C(sp3)-H Cross-Coupling of Benzamides with Amides by Nickel Catalysis
    Lv, Ningning
    Yu, Shuling
    Hong, Chao
    Han, De-Man
    Zhang, Yuhong
    ORGANIC LETTERS, 2020, 22 (23) : 9308 - 9312
  • [10] Ligand-Enabled γ-C(sp3)-H Cross-Coupling of Nosyl-Protected Amines with Aryl- and Alkylboron Reagents
    Shao, Qian
    He, Jian
    Wu, Qing-Feng
    Yu, Jin-Quan
    ACS CATALYSIS, 2017, 7 (11): : 7777 - 7782
12345