Catalytic tert-alkylation of enamides via C-C bond cleavage under photoredox conditions

被引：0
|
作者：
Tsuchiya, Naoki [1 ]
Oku, Ayane [1 ]
Nishikata, Takashi [1 ]
机构：
[1] Yamaguchi Univ, Grad Sch Sci & Engn, 2-16-1 Tokiwadai, Ube, Yamaguchi 7558611, Japan
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 52期
关键词：
CARBOXYLIC-ACIDS; TRIFLUOROMETHYLTHIOLATION; DICARBOFUNCTIONALIZATION; DEOXYGENATION; RADICALS; ALCOHOLS;
D O I：
10.1039/d4cc01643b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Efficient C-C bond cleavage is recognized as a persistent challenge in the field of synthetic methodology. In this study, we found that tertiary alkyl radicals are smoothly formed from tertiary alkylated dienones (BHT adducts) via SET, using PDI as a photocatalyst. Resulting tert-alkyl radicals could be applied to the tert-alkylation of enamides. The driving force of this C-C bond cleavage reaction is the mesolytic cleavage of the BHT adducts. The mechanistic study revealed that PDI anion radical is the key active species during the catalytic cycle.
引用
收藏
页码：6623 / 6626
页数：4
相关论文
共 50 条
  • [1] Stereoselective cyclopropanation of enamides via C-C bond cleavage of cyclopropenes
    Chen, Jie
    Han, Jiabin
    Wu, Tao
    Zhang, Jian
    Li, Meng
    Xu, Ying
    Zhang, Jinli
    Jiao, Yongjuan
    Yang, Yanhui
    Jiang, Yaojia
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07) : 1820 - 1825
  • [2] Homogeneous Catalytic Oxidation of Light Alkanes: C-C Bond Cleavage under Mild Conditions
    Chepaikin, E. G.
    Bezruchenko, A. P.
    Menchikova, G. N.
    Moiseeva, N. I.
    Gekhman, A. E.
    [J]. KINETICS AND CATALYSIS, 2010, 51 (05) : 666 - 671
  • [3] Homogeneous catalytic oxidation of light alkanes: C-C bond cleavage under mild conditions
    E. G. Chepaikin
    A. P. Bezruchenko
    G. N. Menchikova
    N. I. Moiseeva
    A. E. Gekhman
    [J]. Kinetics and Catalysis, 2010, 51 : 666 - 671
  • [4] Oxidative C-C Bond Cleavage of Aldehydes via Visible-Light Photoredox Catalysis
    Sun, Hongnan
    Yang, Chao
    Gao, Fei
    Li, Zhe
    Xia, Wujiong
    [J]. ORGANIC LETTERS, 2013, 15 (03) : 624 - 627
  • [5] Transforming cyclopropanes to enamides via σ-C-C bond eliminative borylation
    Kang, Shuyu
    Lv, Jiahang
    Wang, Tianhang
    Wu, Bingcheng
    Wang, Minyan
    Shi, Zhuangzhi
    [J]. NATURE COMMUNICATIONS, 2024, 15 (01)
  • [6] C-C bond cleavage arylation and alkenylation of cyclobutanone oxime ethers via photoredox/nickel catalysis
    Peng, Chenglin
    Tang, Yingru
    Sun, Shili
    Wei, Yu
    Zhou, Weiji
    Guo, Li-Na
    Xu, Liang
    Liu, Shuai
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024, : 6104 - 6109
  • [7] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
    Dong, Guangbin
    [J]. TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
  • [8] Asymmetric Transformations via C-C Bond Cleavage
    Souillart, Laetitia
    Parker, Evelyne
    Cramer, Nicolai
    [J]. C-C BOND ACTIVATION, 2014, 346 : 163 - 193
  • [9] Shining Light on C-S Bonds: Recent Advances in C-C Bond Formation Reactions via C-S Bond Cleavage under Photoredox Catalysis
    Gao, Jian
    Feng, Jie
    Du, Ding
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (22) : 3637 - 3659
  • [10] A General Synthesis of Ynones from Aldehydes via Oxidative C-C bond Cleavage under Aerobic Conditions
    Wang, Zhaofeng
    Li, Li
    Huang, Yong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (35) : 12233 - 12236
12345