Electrochemical oxidative C(sp3)-H/O-H cross-coupling for the synthesis of α-acyloxyketones

被引:6
作者
Wu, Jiwei [1 ,2 ]
Shi, Haowen [1 ]
Liu, Jianguo [1 ]
Wang, Ruiyou [1 ]
Zhou, Jie [2 ]
Xu, Xiao-Lan [3 ]
Xu, Hua-Jian [2 ]
机构
[1] Anhui Sci & Technol Univ, Coll Chem & Mat Engn, Fengyang 233100, Peoples R China
[2] Hefei Univ Technol, Inst Ind & Equipment Technol, Sch Chem & Chem Engn, Sch Food & Biol Engn, Hefei 230009, Peoples R China
[3] Anhui Med Univ, Sch Med Sci, Hefei 230009, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 10期
关键词
ONE-POT SYNTHESIS; CARBONYL-COMPOUNDS; CARBOXYLIC-ACIDS; KETONES; ACYLOXYLATION; ACETOXYLATION; OXYACYLATION; ACCESS; OXO; FUNCTIONALIZATION;
D O I
10.1039/d3qo00204g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C(sp(3))-H/O-H cross-coupling represents an ideal strategy for constructing C(sp(3))-O bonds but remains challenging due to the relatively inert C(sp(3))-H bonds. Herein, we report a facile and novel electrochemical oxidative C(sp(3))-H/O-H cross-coupling method, leading to various useful a-acyloxyketones with moderate to excellent yields under transition metal- and oxidant-free conditions. A series of carboxylic acids including aromatic and aliphatic acids and ketones are compatible with this reaction.
引用
收藏
页码:2459 / 2464
页数:6
相关论文
共 57 条
  • [1] Electrochemical Benzylic C(sp3)-H Acyloxylation
    Atkins, Alexander P.
    Rowett, Albert C.
    Heard, David M.
    Tate, Joseph A.
    Lennox, Alastair J. J.
    [J]. ORGANIC LETTERS, 2022, : 5105 - 5108
  • [2] Molecular interactions of new pregnenedione derivatives
    Bratoeff, E
    Ramírez, E
    Flores, E
    Valencia, N
    Sánchez, M
    Heuze, I
    Cabeza, M
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) : 1132 - 1136
  • [3] Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers
    Bu, Faxiang
    Lu, Lijun
    Hu, Xia
    Wang, Shengchun
    Zhang, Heng
    Lei, Aiwen
    [J]. CHEMICAL SCIENCE, 2020, 11 (36) : 10000 - 10004
  • [4] One-pot synthesis of α-acyloxycarbonyl compounds via oxidative decarboxylation coupling reaction of α-oxo carboxylic acids with carbonyl compounds
    Chang, Li-Ming
    Yuan, Gao-Qing
    [J]. TETRAHEDRON, 2016, 72 (44) : 7003 - 7007
  • [5] Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis
    Cheng, Xu
    Lei, Aiwen
    Mei, Tian-Sheng
    Xu, Hai-Chao
    Xu, Kun
    Zeng, Chengchu
    [J]. CCS CHEMISTRY, 2022, 4 (04): : 1120 - 1152
  • [6] α-Hydroxylation of β-dicarbonyl compounds
    Christoffers, J
    Baro, A
    Werner, T
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) : 143 - 151
  • [7] Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones
    Fu, Niankai
    Li, Longji
    Yang, Qi
    Luo, Sanzhong
    [J]. ORGANIC LETTERS, 2017, 19 (08) : 2122 - 2125
  • [8] A simple and efficient approach to realize difunctionalization of arylketones with malonate esters via electrochemical oxidation
    Gao, Huihui
    Zha, Zhenggen
    Zhang, Zhenlei
    Ma, Huanyue
    Wang, Zhiyong
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (39) : 5034 - 5036
  • [9] The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols
    Guo, Songjin
    Yu, Jin-Tao
    Dai, Qiang
    Yang, Haitao
    Cheng, Jiang
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (47) : 6240 - 6242
  • [10] Anodic benzylic C(sp3)-H amination: unified access to pyrrolidines and piperidines
    Herold, Sebastian
    Bafaluy, Daniel
    Muniz, Kilian
    [J]. GREEN CHEMISTRY, 2018, 20 (14) : 3191 - 3196