Photocatalytic fluorosulfonylation of aliphatic carboxylic acid NHPI esters

被引:0
|
作者
Zhang, Honghai [1 ]
Li, Shaojie [1 ]
Zheng, Han-Liang [2 ]
Zhu, Gangguo [2 ]
Liao, Saihu [1 ,3 ]
Nie, Xingliang [1 ,2 ]
机构
[1] Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou,350108, China
[2] Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua,321004, China
[3] Beijing National Laboratory of Molecular Science (BNLMS), Beijing,100190, China
基金
中国国家自然科学基金;
关键词
Carboxylic acids - Esters - Fluorine compounds;
D O I
暂无
中图分类号
学科分类号
摘要
Sulfonyl fluorides have been increasingly favored by medicinal chemists and chemical biologists because of their unique reactivity and stability, but their synthetic methods still have certain limitations. Based on the SO2 radical insertion/fluorination strategy, we have developed a novel method for photocatalytic induced synthesis of alkylsulfonyl fluorides (low to 1 mol% P.C. and up to 92% yield), which covers primary, secondary and tertiary aliphatic carboxylic acid NHPI esters, providing a facile method for the late-stage fluorosulfonylation of natural products and drugs. This method provides an efficient and reliable approach for the synthesis and application of alkylsulfonyl fluorides. © 2022 The Royal Society of Chemistry.
引用
收藏
页码:4854 / 4860
相关论文
共 50 条
  • [1] Photocatalytic fluorosulfonylation of aliphatic carboxylic acid NHPI esters
    Zhang, Honghai
    Li, Shaojie
    Zheng, Han-Liang
    Zhu, Gangguo
    Liao, Saihu
    Nie, Xingliang
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18): : 4854 - 4860
  • [2] Aliphatic sulfonyl fluoride synthesis via reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acid NHPI esters
    Ma, Zhanhu
    Liu, Yongan
    Ma, Xiaoyu
    Hu, Xiaojun
    Guo, Yong
    Chen, Qing-Yun
    Liu, Chao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (04) : 1115 - 1120
  • [3] Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids
    Yi, Ji-Tao
    Zhou, Xiang
    Chen, Qi-Long
    Chen, Zhi-Da
    Lu, Gui
    Weng, Jiang
    CHEMICAL COMMUNICATIONS, 2022, 58 (67) : 9409 - 9412
  • [4] Structure and reactivity in the hydrolyses of aliphatic carboxylic acid esters and chlorides
    Regan, Andrew C.
    Watt, C. Ian F.
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2007, 20 (03) : 180 - 189
  • [5] Syntheses of α-monofluoroalkyl acetophenones from fluoroalkyl carboxylic NHPI esters and silyl enol ethers by photocatalytic decarboxylative reaction
    Kou, Min
    Zheng, Jianli
    Chen, Tong
    Wu, Yanghao
    Huang, Ling
    Cao, Dongdong
    Chen, Dingben
    JOURNAL OF FLUORINE CHEMISTRY, 2024, 276
  • [6] ALIPHATIC AND ALICYCLIC CARBOXYLIC ESTERS OF LEVONORGESTREL
    SHAFIEE, A
    VOSSOGHI, M
    SAVABI, F
    WATSON, TG
    SCHUBERT, K
    PONSOLD, K
    WERNER, W
    WAGNER, H
    VLAHOV, R
    TARPANOV, V
    BOSHKOVALJAPOVA, M
    MILENKOV, B
    STOILOVA, V
    VLAHOV, J
    SNATZKE, G
    DUDDECK, H
    STEROIDS, 1983, 41 (03) : 349 - 359
  • [7] Utilization of photocatalysts in decarboxylative coupling of carboxylic N-hydroxyphthalimide (NHPI) esters
    Zhang, Yajing
    Ma, Donglai
    Zhang, Zipeng
    ARABIAN JOURNAL OF CHEMISTRY, 2022, 15 (07)
  • [8] ALPHA-SILYL TRIMETHYLSILYL ESTERS FROM ALIPHATIC CARBOXYLIC-ACID DIANIONS
    BELLASSOUED, M
    DUBOIS, JE
    BERTOUNESQUE, E
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1988, 97 (04): : 263 - 266
  • [9] KINETIC RELATIONSHIPS OF ACIDOLYSIS OF METHYL ESTERS OF ALIPHATIC CARBOXYLIC ACIDS BY ACRYLIC ACID.
    Chubarov, G.A.
    Danov, S.M.
    Logutov, V.I.
    Obmelyukhina, T.N.
    Journal of applied chemistry of the USSR, 1984, 57 (6 pt 2): : 1229 - 1233
  • [10] The formation of carbonic acid esters and carboxylic acid esters
    Baur, E
    Namek, M
    HELVETICA CHIMICA ACTA, 1940, 23 : 1101 - 1110