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

被引:47
|
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
  • [21] Remote C-H Functionalizations by Ruthenium Catalysis
    Ackermann, Lutz
    Samanta, Ramesh C.
    Rogge, Torben
    Ackermann, Lutz
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (17): : 2911 - 2934
  • [22] Sequential Selective C-H and C(sp3)-+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds
    Babu, K. Naresh
    Massarwe, Fedaa
    Shioukhi, Israa
    Masarwa, Ahmad
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (50) : 26199 - 26209
  • [23] Regioselective Sulfonylvinylation of the Unactivated C(sp3)-H Bond via a C-Centered Radical-Mediated Hydrogen Atom Transfer (HAT) Process
    Yang, Shan
    Wu, Xinxin
    Wu, Shuo
    Zhu, Chen
    [J]. ORGANIC LETTERS, 2019, 21 (12) : 4837 - 4841
  • [24] Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
    An, Qing
    Wang, Ziyu
    Chen, Yuegang
    Wang, Xin
    Zhang, Kaining
    Pan, Hui
    Liu, Weimin
    Zuo, Zhiwei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (13) : 6216 - 6226
  • [25] Intramolecular Hydrogen Atom Transfer from Unactivated C(sp3)-H Bond to Alkyl Radical
    Liu, Huiying
    Jin, Qihao
    Wu, Xinxin
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (08)
  • [26] Electrochemical C(sp3)-H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent
    Morii, Yuma
    Watanabe, Taito
    Saga, Yutaka
    Kambe, Tetsuya
    Kondo, Mio
    Masaoka, Shigeyuki
    [J]. CHEMELECTROCHEM, 2024, 11 (10)
  • [27] Metal-free photoinduced hydrogen atom transfer assisted C(sp3)-H thioarylation
    Grover, Jagrit
    Prakash, Gaurav
    Teja, Chitrala
    Lahiri, Goutam Kumar
    Maiti, Debabrata
    [J]. GREEN CHEMISTRY, 2023, 25 (09) : 3431 - 3436
  • [28] Electronic control over site-selectivity in hydrogen atom transfer (HAT) based C(sp3)-H functionalization promoted by electrophilic reagents
    Galeotti, Marco
    Salamone, Michela
    Bietti, Massimo
    [J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (06) : 2171 - 2223
  • [29] Diverse sp3 C-H functionalization through alcohol β-sulfonyloxylation
    Xu, Yan
    Yan, Guobing
    Ren, Zhi
    Dong, Guangbin
    [J]. NATURE CHEMISTRY, 2015, 7 (10) : 829 - 834
  • [30] Catalytic C-H activation of sp3 C-H bonds in α-position to a nitrogen atom -: Two new approaches
    Doye, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (18) : 3351 - +