A selective and mild electrochemical defluorinative carboxylation for late-stage C(sp3)-F bond functionalization

被引:8
|
作者
Mondal, Subhojit [1 ]
Sarkar, Soumik [1 ]
Wang, Jason W. [1 ]
Meanwell, Michael W. [1 ]
机构
[1] Univ Alberta, Dept Chem, 11227 Saskatchewan Dr NW, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
DEFLUOROALKYLATION; ACIDS;
D O I
10.1039/d3gc03387b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the first general protocol for the electrochemical defluorinative carboxylation of trifluoromethyl (hetero)arenes, and trifluoromethyl-acetates and -acetamides, for accessing their highly valuable alpha,alpha-difluorocarboxylic acid analogues. Given the immense synthetic versatility of carboxylic acids, our new protocol may become a useful tool for accessing novel fluorinated analogues in drug design and agrochemical development.
引用
收藏
页码:9075 / 9079
页数:5
相关论文
共 50 条
  • [1] Site Selective Chlorination of C(sp3)-H Bonds Suitable for Late-Stage Functionalization
    Fawcett, Alexander
    Keller, M. Josephine
    Herrera, Zachary
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (15) : 8276 - 8283
  • [2] Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles
    Zhe Chang
    Jialin Huang
    Si Wang
    Geshuyi Chen
    Heng Zhao
    Rui Wang
    Depeng Zhao
    Nature Communications, 12
  • [3] Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles
    Chang, Zhe
    Huang, Jialin
    Wang, Si
    Chen, Geshuyi
    Zhao, Heng
    Wang, Rui
    Zhao, Depeng
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [4] Manganese-catalysed benzylic C(sp3)–H amination for late-stage functionalization
    Joseph R. Clark
    Kaibo Feng
    Anasheh Sookezian
    M. Christina White
    Nature Chemistry, 2018, 10 : 583 - 591
  • [5] Manganese-catalysed benzylic C(sp3)-H amination for late-stage functionalization
    Clark, Joseph R.
    Feng, Kaibo
    Sookezian, Anasheh
    White, M. Christina
    NATURE CHEMISTRY, 2018, 10 (06) : 583 - 591
  • [6] Late-stage oxidative C(sp3)-H methylation
    Feng, Kaibo
    Quevedo, Raundi E.
    Kohrt, Jeffrey T.
    Oderinde, Martins S.
    Reilly, Usa
    White, M. Christina
    NATURE, 2020, 580 (7805) : 621 - +
  • [7] Late-stage oxidative C(sp3)–H methylation
    Kaibo Feng
    Raundi E. Quevedo
    Jeffrey T. Kohrt
    Martins S. Oderinde
    Usa Reilly
    M. Christina White
    Nature, 2020, 580 : 621 - 627
  • [8] Exploring Electrochemical C(sp3)-H Oxidation for the Late-Stage Methylation of Complex Molecules
    Novaes, Luiz F. T.
    Ho, Justin S. K.
    Mao, Kaining
    Liu, Kaida
    Tanwar, Mayank
    Neurock, Matthew
    Villemure, Elisia
    Terrett, Jack A.
    Lin, Song
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (03) : 1187 - 1197
  • [9] Asymmetric allylic C(sp3)-C(sp3) bond functionalization
    He, Zhi-Tao
    NATURE SYNTHESIS, 2024, 3 (08): : 941 - 942
  • [10] Late-Stage β-C(sp3)-H Deuteration of Carboxylic Acids
    Uttry, Alexander
    Mal, Sourjya
    van Gemmeren, Manuel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (29) : 10895 - 10901