Aerobic Oxidation of Benzylic sp3 C-H Bonds through Cooperative Visible-Light Photoredox Catalysis of N-Hydroxyimide and Dicyanopyrazine

被引:46
|
作者
Liu, Xinfei [1 ]
Lin, Lu [1 ]
Ye, Xinyi [2 ]
Tan, Choon-Hong [2 ]
Jiang, Zhiyong [1 ]
机构
[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Jinming Campus, Kaifeng 475004, Henan, Peoples R China
[2] Nanyang Technol Univ, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore
关键词
cooperative catalysis; carbonyls; n-hydroxyimides; photo-oxygenation; visible-light photocatalysis; PHOTOCATALYTIC OXYGENATION; SELECTIVE OXIDATION; ELECTRON-TRANSFER; SOLVENT-FREE; HYDROCARBONS; FUNCTIONALIZATION; PHOTOOXYGENATION; PHOTOOXIDATION; ACTIVATION; ALCOHOLS;
D O I
10.1002/ajoc.201600426
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-driven cooperative catalysis between dicyanopyrazine-derived chromophore (DPZ) and N-hydroxyimide has been developed. Under irradiation with a low-energy and operationally convenient visible light, the cooperative catalytic system could facilitate the aerobic oxygenation of a series of benzylic sp(3) C-H bonds through a photoredox pathway. The method provides a novel approach to access valuable carbonyls from benzylic methylenes and benzylic alcohols in moderate to excellent yields (up to 93%).
引用
收藏
页码:422 / 425
页数:4
相关论文
共 50 条
  • [1] Visible-Light Induced Trifluoromethylation of Internal Olefmic C-H Bonds through Photoredox Catalysis
    Gou Baoquan
    Yang Chao
    Zhang Lei
    Xia Wujiong
    ACTA CHIMICA SINICA, 2017, 75 (01) : 66 - 69
  • [2] Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Mondal, Pradip Kumar
    CHEMICAL COMMUNICATIONS, 2019, 55 (65) : 9689 - 9692
  • [3] Oxidation induced C(sp3)-O cleavage via visible-light photoredox catalysis
    Wang, Shengchun
    Liu, Jiamei
    Niu, Linbin
    Yi, Hong
    Chiang, Chien-Wei
    Lei, Aiwen
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2018, 355 : 120 - 124
  • [4] C(sp3)-H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis
    Wakaki, Takayuki
    Sakai, Kentaro
    Enomoto, Takafumi
    Kondo, Mio
    Masaoka, Shigeyuki
    Oisaki, Kounosuke
    Kanai, Motomu
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (32) : 8051 - 8055
  • [5] The functionalization of a cascade of C(sp2)-H/C(sp3)-H bonds: synthesis of fused dihydropyrazoles via visible-light photoredox catalysis
    Cheng, Jian
    Xu, Pan
    Li, Weipeng
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2016, 52 (80) : 11901 - 11904
  • [6] Visible-Light Photocatalysed Cyanation of Benzylic C-H Bonds
    Singh, Satya Prakash
    Singh, Praveen P.
    Gahtori, Prashant
    Singh, Shailendra
    Srivastava, Vishal
    CROATICA CHEMICA ACTA, 2024, 97 (01) : 43 - 48
  • [7] Ferric nitrate-catalyzed aerobic oxidation of benzylic sp3 C-H bonds of ethers and alkylarenes
    Hong, Chao
    Ma, Jiaqi
    Li, Meichao
    Jin, Liqun
    Hu, Xinquan
    Mo, Weimin
    Hu, Baoxiang
    Sun, Nan
    Shen, Zhenlu
    TETRAHEDRON, 2017, 73 (21) : 3002 - 3009
  • [8] Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Singh, Deepak
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 7161 - 7171
  • [9] Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst
    Zhang, Zhiguang
    Gao, Yuan
    Liu, Yuan
    Li, Jianjun
    Xie, Hexin
    Li, Hao
    Wang, Wei
    ORGANIC LETTERS, 2015, 17 (21) : 5492 - 5495
  • [10] The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis
    Cuthbertson, James D.
    MacMillan, David W. C.
    NATURE, 2015, 519 (7541) : 74 - 77