β-C(sp3) -H chlorination of amide derivatives via photoinduced copper charge transfer catalysis

被引:9
|
作者
He, Yuhang [1 ]
Tian, Chao [1 ]
An, Guanghui [1 ]
Li, Guangming [1 ]
机构
[1] Heilongjiang Univ, Sch Chem & Mat Sci, Key Lab Funct Inorgan Mat Chem, MOE, Harbin 150080, Peoples R China
关键词
Photoinduced copper catalysis; Ligand-to-metal charge transfer; 1,4-Hydrogen atom transfer; beta-Halogenated amide; Late-stage functionalization; PD(II)-CATALYZED BROMINATION; AMINO-ACIDS; FLUORINATION; KETONES; BONDS; IODINATION; CU2O;
D O I
10.1016/j.cclet.2023.108546
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An atom economic beta-C(sp(3))-H chlorination of amide derivatives has been developed. This mild protocol employs CuCl2 instead of palladium catalysts with atom-economic HCl as chlorine sources and enables the late-stage functionalization of medicine derivatives. Mechanism studies suggest a plausible visible light triggered ligand-to-metal charge transfer (LMCT)/1,4-hydrogen atom transfer (HAT) cascade.
引用
收藏
页数:5
相关论文
共 50 条
  • [11] Iron-catalyzed thiolation of C(sp3)-H with sulfonyl chlorides via photoinduced ligand-to-metal charge transfer
    Liu, Sheng-Ping
    Yang, Lan
    He, Yan-Hong
    Guan, Zhi
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (24): : 7001 - 7010
  • [12] Benzylic C(sp3)-H Azidation: Copper vs Iron Catalysis
    Renteria-Gomez, Angel
    Torres-Ochoa, Ruben O.
    Palamini, Pierre
    Simonet-Davin, Raphael
    Wang, Qian
    Waser, Jerome
    Zhu, Jieping
    HELVETICA CHIMICA ACTA, 2024, 107 (03)
  • [13] Direct Synthesis of β-Amino Boronates via Amide α-C-H Bond Activation and C(sp3)-C(sp3) Coupling under Dual Ni/Photoredox Catalysis
    Hu, Zihao
    Wang, Dong
    Xu, Tao
    ACS CATALYSIS, 2023, 14 (01): : 547 - 553
  • [14] Copper-catalyzed transfer methylenation via C(sp3)-C(sp3) bond cleavage of alcohols
    Hong, Chuan-Ming
    Zhuang, Xin
    Luo, Zhen
    Xiong, Si-Qi
    Liu, Zheng-Qiang
    Li, Qing-Lin
    Zou, Fei-Fei
    Li, Qing-Hua
    Liu, Tang-Lin
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6547 - 6555
  • [15] Direct Synthesis of β-Amino Boronates via Amide α-C-H Bond Activation and C(sp3)-C(sp3) Coupling under Dual Ni/Photoredox Catalysis
    Hu, Zihao
    Wang, Dong
    Xu, Tao
    ACS Catalysis, 2024, 14 (01) : 547 - 553
  • [16] Photoinduced C(sp3)-H borylation of alkanes mediated by copper(ii) chloride
    Fang, Wen
    Wang, Huai-Qin
    Zhou, Wei
    Luo, Zhi-Wen
    Dai, Jian-Jun
    CHEMICAL COMMUNICATIONS, 2023, 59 (46) : 7108 - 7111
  • [17] FeCl3-Catalyzed C(sp3)-H Heteroarylation Enabled by Photoinduced Ligand-to-Metal Charge Transfer
    Li, Pengcheng
    Tu, Jia-Lin
    Gao, Han
    Shi, Chengcheng
    Zhu, Yining
    Guo, Lin
    Yang, Chao
    Xia, Wujiong
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (02) : 220 - 224
  • [18] Allylic C(sp3)–H arylation of olefins via ternary catalysis
    Huan-Ming Huang
    Peter Bellotti
    Pan-Pan Chen
    Kendall N. Houk
    Frank Glorius
    Nature Synthesis, 2022, 1 : 59 - 68
  • [19] Allylic C(sp3)-H arylation of olefins via ternary catalysis
    Huang, Huan-Ming
    Bellotti, Peter
    Chen, Pan-Pan
    Houk, Kendall N.
    Glorius, Frank
    NATURE SYNTHESIS, 2022, 1 (01): : 59 - 68
  • [20] C(sp3)-H Carboxylation via Carbene/Photoredox Cooperative Catalysis
    Schull, Cullen R.
    Cao, Jing
    Mitton-Fry, Sophia R.
    Mrksich, Mara
    Scheidt, Karl A.
    ACS CATALYSIS, 2025, 15 (02): : 1287 - 1293