Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

被引:163
|
作者
Kautzky, Jacob A. [1 ]
Wang, Tao [1 ]
Evans, Ryan W. [1 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; FLUORINE; ALKYLATION; RADICALS; CF3;
D O I
10.1021/jacs.8b02650
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.
引用
收藏
页码:6522 / 6526
页数:5
相关论文
共 50 条
  • [1] Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
    Tan, Xinqiang
    Liu, Zhonglin
    Shen, Haigen
    Zhang, Pei
    Zhang, Zhenzhen
    Li, Chaozhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) : 12430 - 12433
  • [2] Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids
    Senaweera, Sameera
    Cartwright, Kaitie C.
    Tunge, Jon A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12553 - 12561
  • [3] Electrophotochemical Decarboxylative Azidation of Aliphatic Carboxylic Acids
    Wang, Yukang
    Li, Liubo
    Fu, Niankai
    ACS CATALYSIS, 2022, 12 (17): : 10661 - 10667
  • [4] Decarboxylative Nucleophilic Fluorination of Aliphatic Carboxylic Acids
    Yu, Qian
    Zhou, Donglin
    Ma, Junjun
    Song, Chunlan
    ORGANIC LETTERS, 2024, 26 (20) : 4257 - 4261
  • [5] Iron-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with Trifluoromethanesulfinate
    Patra, Tuhin
    Deb, Arghya
    Manna, Srimanta
    Sharma, Upendra
    Maiti, Debabrata
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5247 - 5250
  • [6] Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis
    Xu, Pan
    Abdukader, Ablimit
    Hu, Kaidong
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2014, 50 (18) : 2308 - 2310
  • [7] NEW DECARBOXYLATIVE CHALCOGENATION OF ALIPHATIC AND ALICYCLIC CARBOXYLIC-ACIDS
    BARTON, DHR
    BRIDON, D
    ZARD, SZ
    TETRAHEDRON LETTERS, 1984, 25 (50) : 5777 - 5780
  • [8] Silver-Catalyzed Decarboxylative Azidation of Aliphatic Carboxylic Acids
    Zhu, Yuchao
    Li, Xinyao
    Wang, Xiaoyang
    Huang, Xiaoqiang
    Shen, Tao
    Zhang, Yiqun
    Sun, Xiang
    Zou, Miancheng
    Song, Song
    Jiao, Ning
    ORGANIC LETTERS, 2015, 17 (19) : 4702 - 4705
  • [9] Iron-Photocatalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids
    Denkler, Luca Mareen
    Shekar, Meghana Aladahalli
    Bunescu, Ala
    SYNLETT, 2025,
  • [10] Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids
    Wang, Zhentao
    Zhu, Lin
    Yin, Feng
    Su, Zhongquan
    Li, Zhaodong
    Li, Chaozhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) : 4258 - 4263