Electroreductive deoxygenative carboxylation of alkyl oxalates with CO2

被引:0
作者
Yuan, Yong [1 ]
Jiang, Hangfei [1 ]
Zhang, Ya-Nan [1 ]
Tao, Yuyan [1 ]
Liu, Xincong [1 ]
Huo, Congde [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
关键词
NI-CATALYZED CARBOXYLATION; ELECTROCHEMICAL CARBOXYLATION; CARBON-DIOXIDE; BONDS; ALCOHOLS; ESTERS; ACIDS; CHLORIDES; ALKENES; HALIDES;
D O I
10.1039/d4gc03452j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An electroreductive deoxygenative carboxylation of alkyl oxalates with CO2 is demonstrated for the first time, which offers a general and scalable method for obtaining various carboxylic acids. This electrochemical method features a broad substrate scope and mild reaction conditions; various secondary benzyl alcohols and non-benzylic alcohols, primary benzyl alcohols and non-benzylic alcohols, and tertiary benzyl alcohols and non-benzylic alcohols can be converted into the corresponding carboxylic acids in good to excellent yields. Importantly, this electroreductive deoxygenative carboxylation reaction also offers a mild and straightforward route to access drug molecules, such as ibuprofen, (+/-) naproxen, fenoprofen, hexaprofen, and biprofen.
引用
收藏
页码:10811 / 10817
页数:7
相关论文
共 50 条
  • [1] Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2
    Borjesson, Marino
    Moragas, Toni
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (24) : 7504 - 7507
  • [2] Electrochemical Reductive Carboxylation of para-Quinone Methides with CO2
    Yan, Yunying
    Li, Haiqiong
    Xie, Fenfen
    Lu, Wenhua
    Zhang, Zhengbing
    Jing, Linhai
    Han, Pan
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3830 - 3836
  • [3] Electroreductive Carboxylation of Propargylic Acetates with CO2: Access to Tetrasubstituted 2,3-Allenoates
    Qin, Jing-Hao
    Xiong, Zhi-Qiang
    Cheng, Chaozhihui
    Hu, Ming
    Li, Jin-Heng
    ORGANIC LETTERS, 2023, 25 (51) : 9176 - 9180
  • [4] Electroreductive Dicarboxylation of Unactivated Skipped Dienes with CO2
    Zhang, Wei
    Liao, Li-Li
    Li, Li
    Liu, Yi
    Dai, Long-Fei
    Sun, Guo-Quan
    Ran, Chuan-Kun
    Ye, Jian-Heng
    Lan, Yu
    Yu, Da-Gang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [5] Ambient Electroreductive Carboxylation of Unactivated Alkyl Chlorides and Polyvinyl Chloride (PVC) Upgrading
    Sarkar, Prasenjit
    Dash, Sandeep
    Krause, Jeanette A.
    Sinha, Soumalya
    Panetier, Julien A.
    Jiang, Jianbing Jimmy
    CHEMSUSCHEM, 2024, 17 (23)
  • [6] Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2
    Liu, Yu
    Cornella, Josep
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (32) : 11212 - 11215
  • [7] Photocatalytic Carboxylation with CO2: A Review of Recent Studies
    Huang, Wei
    Lin, Junyue
    Deng, Fei
    Zhong, Hong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (07)
  • [8] Copper-Catalyzed Carboxylation of C-F Bonds with CO2
    Yan, Si-Shun
    Wu, Dong-Shan
    Ye, Jian-Heng
    Gong, Li
    Zeng, Xin
    Ran, Chuan-Kun
    Gui, Yong-Yuan
    Li, Jing
    Yu, Da-Gang
    ACS CATALYSIS, 2019, 9 (08) : 6987 - 6992
  • [9] Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water
    Gaydou, Morgane
    Moragas, Toni
    Julia-Hernandez, Francisco
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (35) : 12161 - 12164
  • [10] Magnesium-Mediated Umpolung Carboxylation of p-Quinone Methides with CO2
    Yan, Yunying
    Hao, Jianjun
    Xie, Fenfen
    Han, Fen
    Jing, Linhai
    Han, Pan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (20) : 14640 - 14648