Divergent defluorocarboxylation of α-CF3 alkenes with formate via photocatalyzed selective mono-or triple C–F bond cleavage

被引：0

作者：

Xing-Yu Wang ^{[1
]}

Pei Xu ^{[1
]}

Wen-Wen Liu ^{[1
]}

Hao-Qiang Jiang ^{[1
]}

Song-Lei Zhu ^{[1
]}

Dong Guo ^{[1
]}

Xu Zhu ^{[1
]}

机构：

[1] Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University

来源：

Science China(Chemistry) | 2024年 / 67卷 / 01期

基金：

中国国家自然科学基金;

关键词：

D O I：

暂无

中图分类号：

O643.36 [催化剂]; O644.1 [光化学];

学科分类号：

070304 ; 081704 ; 081705 ;

摘要：

Unprecedented divergent synthesis of gem-difluorovinylacetic acid and glutaric acid derivatives from α-CF3alkenes with formate as the carbonyl source was disclosed.The reaction can undergo selective mono-or triple C-F bond cleavage by simply switching the photocatalyst and hydrogen atom transfer(HAT) catalyst under visible-light-induced conditions at room temperature.Foramte acts as both the C1 source and the reductant through the generation of CO2·-species,which underwent Giese radical addition to electron-deficient alkenes to trigger the consecutive C-F bond cleavage and carboxylation process.

引用

页码：368 / 373

页数：6

共 50 条

[41] Influence of F and CF3 Groups at the C=C Double Bond on the Structure and Properties of Olefinic‐Series Compounds in the Gas Phase: an ab initio MP2 Study
Yu. A. Borisov
Journal of Structural Chemistry, 2002, 43 : 734 - 742
[42] C-F bond activation of perfluoroalkenes by ruthenium phosphine hydride complexes:: X-ray crystal structures of cis-Ru(dmpe)2F(F•••HF) and [Ru(dcpe)2H]+[(CF3)2C=C(O)CF2CF3]-
Kirkham, MS
Mahon, MF
Whittlesey, MK
CHEMICAL COMMUNICATIONS, 2001, (09) : 813 - 814
[43] Synthesis of Seven-membered Ring Containing Difluoromethylene Unit by Sc(OTf)3-catalyzed Activation of Single C-F Bond in CF3 Group
Hisano, Naoya
Kimura, Daiki
Mori, Keiji
CHEMISTRY LETTERS, 2019, 48 (08) : 771 - 774
[44] Organo-photoredox catalyzed gem-difluoroallylation of ketone-derived dihydroquinazolinones via C(sp3)-C bond and C(sp3)-F bond cleavage
Zhang, Yue
Zhu, Tianshuai
Lin, Yuqian
Wei, Xian
Xie, Xinyu
Lin, Ruofan
Zhang, Zhijie
Fang, Weiwei
Zhang, Jing-Jing
Zhang, Yue
Hu, Meng-Yang
Cai, Lingchao
Chen, Zhen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (27) : 5561 - 5568
[45] Selective synthesis of poly-substituted fluorine-containing pyridines and dihydropyrimidines via cascade C-F bond cleavage protocol
Chen, Zixian
Zhu, Jiangtao
Xie, Haibo
Li, Shan
Wu, Yongming
Gong, Yuefa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5682 - 5691
[46] New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp3)-F Bond Cleavage
Roy, Sourav
Besset, Tatiana
JACS AU, 2025, 5 (02): : 466 - 485
[47] Copper-catalyzed gem -difluoroolefination of diazo compounds with TMSCF3 via C-F bond cleavage
Hu, J. (jinbohu@sioc.ac.cn), 1600, American Chemical Society (135):
[48] Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C-S bond cleavage
Liu, Xianqin
Li, Xufeng
Wang, Linyuan
Shi, Yongjia
Lv, Jian
Yang, Daoshan
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (08) : 2195 - 2200
[49] Influence of F and CF3 groups at the C=C double bond on the structure and properties of protonated forms of olefin-series compounds:: An MP2 ab initio study
Borisov, YA
JOURNAL OF STRUCTURAL CHEMISTRY, 2002, 43 (05) : 743 - 749
[50] Influence of F and CF3 groups at the C=C double bond on the structure and properties of olefinic-series compounds in the gas phase:: An ab initio MP2 study
Borisov, YA
JOURNAL OF STRUCTURAL CHEMISTRY, 2002, 43 (05) : 734 - 742

← 1 2 3 4 5 →