Free Carboxylic Acids: The Trend of Radical Decarboxylative Functionalization

被引:48
|
作者
Li, Liubo [1 ,2 ]
Yao, Yan [1 ,2 ,3 ]
Fu, Niankai [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Funct Inst Chem, Beijing 100190, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
decarboxylative functionalization; electrochemistry; electrophotochemistry; ligand-to-metal charge transfer (LMCT); photoredox; ALPHA-AMINO-ACIDS; TRANSITION-METAL; OXIDATIVE DECARBOXYLATION; ELECTROCHEMICAL OXIDATION; KINETIC CHARACTERISTICS; AROYLOXYL RADICALS; RECENT PROGRESS; PHOTOREDOX; LIGHT; ALKYLATION;
D O I
10.1002/ejoc.202300166
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The exceptional versatility of carboxylic acids has been extensively exploited in organic synthesis across several decades. There has been a recent upsurge of radical decarboxylative transformations. The process can be initiated under mild conditions, and the resultant radicals have orthogonal reactivities to closed-shell species, thus providing immense opportunities for streamlining novel reactions. The use of free carboxylic acids is the most desirable owing to its high atom and step economy. Aiming to demonstrate the attractiveness of the strategy and to inspire chemists to tackle existing challenges, this review outlines the recent advances on radical decarboxylative functionalization of free carboxylic acids.
引用
收藏
页数:14
相关论文
共 50 条
  • [21] Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
    Kautzky, Jacob A.
    Wang, Tao
    Evans, Ryan W.
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (21) : 6522 - 6526
  • [22] Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids
    Senaweera, Sameera
    Cartwright, Kaitie C.
    Tunge, Jon A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12553 - 12561
  • [23] Decarboxylative Etherification of Aromatic Carboxylic Acids
    Bhadra, Sukalyan
    Dzik, Wojciech I.
    Goossen, Lukas J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) : 9938 - 9941
  • [24] Electrochemical Decarboxylative Oxygenation of Carboxylic Acids
    Meng, Xiangtai
    Xu, Hehua
    Zheng, Yu
    Luo, Jinyue
    Huang, Shenlin
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (15) : 5067 - 5071
  • [25] Silver-catalyzed decarboxylative C–H functionalization of cyclic aldimines with aliphatic carboxylic acids
    Jingjing Wang
    Xue Liu
    Ziyan Wu
    Feng Li
    Tingting Qin
    Siyuan Zhang
    Weiguang Kong
    Lantao Liu
    Chinese Chemical Letters, 2021, 32 (09) : 2777 - 2781
  • [26] Photoinduced decarboxylative borylation of carboxylic acids
    Fawcett, Alexander
    Pradeilles, Johan
    Wang, Yahui
    Mutsuga, Tatsuya
    Myers, Eddie L.
    Aggarwal, Varinder K.
    SCIENCE, 2017, 357 (6348) : 283 - 286
  • [27] Direct Decarboxylative Functionalization of Carboxylic Acids via O-H Hydrogen Atom Transfer
    Na, Christina G.
    Ravelli, Davide
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (01) : 44 - 49
  • [28] Radical Decarboxylative Cyanomethylation of Aliphatic Carboxylic Acids and Uronic Acids via Vinyl Azide Cascade Fragmentation
    Xu, Linhua
    Li, Qishuai
    Li, Dongwei
    Zhou, Xin
    Song, Ni
    Wang, Peng
    Li, Ming
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (10): : 1191 - 1197
  • [29] Transition-metal-free decarboxylative ipso amination of aryl carboxylic acids
    Zhang, Jing
    Hou, Ye-Xing
    Tang, Yan-Liu
    Xu, Ji-Hang
    Liu, Zi-Kui
    Gao, Yang
    Hu, Xiao-Qiang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13) : 3434 - 3439
  • [30] Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution
    Liu, Chao
    Wang, Xiaoqing
    Li, Zhaodong
    Cui, Lei
    Li, Chaozhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (31) : 9820 - 9823