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
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
收藏
页码:368 / 373
页数:6
相关论文
共 50 条
  • [1] Divergent defluorocarboxylation of α-CF3 alkenes with formate via photocatalyzed selective mono- or triple C-F bond cleavage
    Wang, Xing-Yu
    Xu, Pei
    Liu, Wen-Wen
    Jiang, Hao-Qiang
    Zhu, Song-Lei
    Guo, Dong
    Zhu, Xu
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (01) : 368 - 373
  • [2] Divergent defluorocarboxylation of α-CF3 alkenes with formate via photocatalyzed selective mono- or triple C-F bond cleavage
    Xing-Yu Wang
    Pei Xu
    Wen-Wen Liu
    Hao-Qiang Jiang
    Song-Lei Zhu
    Dong Guo
    Xu Zhu
    Science China Chemistry, 2024, 67 (1) : 368 - 373
  • [3] Synthesis of 5-Fluoro-dihydroindolizines from Pyrrole-2-acetic Acidsand Trifluoromethyl Alkenes via Dual C-F Bond Cleavage in a CF3 Group
    Sun, Zhengchang
    Zhou, Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07): : 4801 - 4812
  • [4] Modular synthesis of α-arylated carboxylic acids, esters and amides via photocatalyzed triple C-F bond cleavage of methyltrifluorides
    Li, Sifan
    Davies, Paul W.
    Shu, Wei
    CHEMICAL SCIENCE, 2022, 13 (22) : 6636 - 6641
  • [5] Metal free and selective activation of one C-F bond in a bound CF3 group
    Azhakar, Ramachandran
    Roesky, Herbert W.
    Wolf, Hilke
    Stalke, Dietmar
    CHEMICAL COMMUNICATIONS, 2013, 49 (18) : 1841 - 1843
  • [6] Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage
    Zhu, Longzhi
    Le, Liyuan
    Yang, Mingpan
    Au, Chak-Tong
    Qiu, Renhua
    Kambe, Nobuaki
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5635 - 5644
  • [7] [4+2] Cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3
    Fu, Yiwei
    Qin, Cong
    Zhang, Zhiqiang
    Shi, Haoyu
    Zhao, Jianbo
    Gong, Xueqing
    Shi, Lei
    Li, Hao
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (16): : 4426 - 4431
  • [8] Single C(sp3)-F Bond Activation in a CF3 Group: Ipso-Defluorooxylation of (Trifluoromethyl)alkenes with Oximes
    Zeng, Hao
    Zhu, Chuanle
    Jiang, Huanfeng
    ORGANIC LETTERS, 2019, 21 (04) : 1130 - 1133
  • [9] Triple ipso-defluoroetherification of (trifluoromethyl)alkenes with fluoroalkylated alcohols: access to fluoroalkylated orthoesters via C(sp3)-F bond cleavage
    Nie, Jia
    Jiang, Huanfeng
    Zhu, Chuanle
    CHEMICAL COMMUNICATIONS, 2023, 59 (53) : 8238 - 8241
  • [10] On the Nature of C?H•••F?C Interactions in Hindered CF3?C(sp3) Bond Rotations
    Prakash, G. K. Surya
    Wang, Fang
    Rahm, Martin
    Shen, Jingguo
    Ni, Chuanfa
    Haiges, Ralf
    Olah, George A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) : 11761 - 11764