Metallaphotoredox catalysis for sp3 C-H functionalizations through hydrogen atom transfer (HAT)

被引:72
|
作者
Zhang, Jingchang [1 ]
Rueping, Magnus [2 ]
机构
[1] Jining Med Univ, Sch Pharm, Dept Chem, Rizhao 276826, Peoples R China
[2] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, KCC, KAUST, Thuwal 239556900, Saudi Arabia
关键词
C(SP(3))-H BONDS; COUPLING REACTION; NICKEL; PHOTOREDOX; ALKYLATION; ARYLATION; COPPER; ALLYLATION; ALDEHYDES; PHOTOELIMINATION;
D O I
10.1039/d3cs00023k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In recent years, the integration of photocatalytic hydrogen atom transfer (HAT) with transition metal catalysis has emerged as a formidable strategy for the construction of C(sp(3))-carbon and C(sp(3))-hetero bonds. The fusion of these two methodologies has been utilized widely in organic synthesis, leading to new transformations in chemical synthesis. In this review, we aim to summarize the recent advances made in sp(3) C-H functionalizations through photocatalytic HAT followed by transition metal catalysis. Our focus will be on the diverse strategies and their synthetic applications, in addition to detailed mechanisms involved in these reactions. An in-depth understanding of these mechanisms is crucial for the rational design of new catalysts and reaction conditions to further enhance the efficiency of these transformations. We hope that this review will serve as a valuable resource for researchers in the area of metallaphotoredox catalysis, and will inspire the further development of this application in green chemistry, drug synthesis, material science, and other related fields.
引用
收藏
页码:4099 / 4120
页数:22
相关论文
共 50 条
  • [1] Metallaphotoredox catalysis for sp3 C-H functionalizations through single-electron transfer
    Zhang, Jingchang
    Rueping, Magnus
    NATURE CATALYSIS, 2024, 7 (09): : 963 - 976
  • [2] Stereoselective benzylic C(sp3)-H alkenylation enabled by metallaphotoredox catalysis
    Li, Yantao
    Bai, Haonan
    Gao, Qi
    Liu, Kai
    Han, Jie
    Li, Weipeng
    Zhu, Chengjian
    Xie, Jin
    CHEMICAL SCIENCE, 2024, 15 (31) : 12511 - 12516
  • [3] Electrochemical C(sp3)-H Functionalization of γ-Lactams Based on Hydrogen Atom Transfer
    Sim, Jeongwoo
    Ryou, Bokyeong
    Choi, Minyeong
    Lee, Changju
    Park, Cheol-Min
    ORGANIC LETTERS, 2022, 24 (23) : 4264 - 4269
  • [4] Acyloxy, sulfate, and phosphate radicals as hydrogen atom transfer (HAT) agents for direct C(sp3)-H functionalization
    Tu, Jia-Lin
    Huang, Binbin
    RSC SUSTAINABILITY, 2024, 2 (11): : 3222 - 3234
  • [5] Direct C-H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis
    Wang, Junlei
    Huang, Binbin
    Gao, Yuan
    Yang, Chao
    Xia, Wujiong
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) : 6895 - 6903
  • [6] Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)-H Acylation Enabled by Metallaphotoredox Catalysis
    Lee, Geun Seok
    Won, Joonghee
    Choi, Seulhui
    Baik, Mu-Hyun
    Hong, Soon Hyeok
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (39) : 16933 - 16942
  • [7] Site-Selective C(sp3)-H Functionalizations Mediated by Hydrogen Atom Transfer Reactions via α-Amino/α-Amido Radicals
    Kaur, Jaspreet
    Barham, Joshua P.
    SYNTHESIS-STUTTGART, 2022, 54 (06): : 1461 - 1477
  • [8] Origin and Regioselectivity of Direct Hydrogen Atom Transfer Mechanism of C(sp3)-H Arylation by [W10O32]4-/Ni Metallaphotoredox Catalysis
    Dong, Yu-Jiao
    Zhu, Bo
    Liang, Yu-Jie
    Guan, Wei
    Su, Zhong-Min
    INORGANIC CHEMISTRY, 2021, 60 (24) : 18706 - 18714
  • [9] Cobalt-catalyzed C(sp2)-H/C(sp3)-H coupling via directed C-H activation and 1,5-hydrogen atom transfer
    Sun, Qiao
    Yoshikai, Naohiko
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 582 - 585
  • [10] Activation Strategies for Alkyl Precursors in Achieving C(sp3)-C(sp3) Cross-Coupling via Metallaphotoredox Catalysis
    Dongbang, Sun
    ORGANOMETALLICS, 2024, 43 (16) : 1662 - 1681