Tri- and di-fluoroethylation of alkenes by visible light photoredox catalysis

被引：16
作者：
Pan, Xiao-Yang [1 ,2 ,3 ]
Zhao, Yue [1 ,2 ,3 ]
Qu, Hong-An [4 ]
Lin, Jin-Hong [3 ]
Hang, Xiao-Chun [1 ,2 ]
Xiao, Ji-Chang [3 ]
机构：
[1] Nanjing Tech Univ NanjingTech, KLOFE, 30 South Puzhu Rd, Nanjing 211800, Jiangsu, Peoples R China
[2] Nanjing Tech Univ NanjingTech, Inst Adv Mat, 30 South Puzhu Rd, Nanjing 211800, Jiangsu, Peoples R China
[3] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[4] Shandong NHU Amino Acid Co Ltd, Xinchang, Zhejiang, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 09期
关键词：
C-H TRIFLUOROETHYLATION; ARYLBORONIC ACIDS; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; 2,2,2-TRIFLUOROETHYLATION; DIFLUOROCARBENE; TRIFLUOROMETHYLATION; DIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; PHARMACEUTICALS;
D O I：
10.1039/c8qo00082d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tri- and di-fluoroethylation of alkenes with sulfonium salts, (Ph2S+CH2RF TfO-) (R-F = CF3 or HCF2), by visible light photoredox catalysis to give tri-/di-fluoroethyl alkenes or methoxytri-/di-fluoroethylation products are described. It was found that varying the reaction solvent led to changes in the reaction path.
引用
收藏
页码：1452 / 1456
页数：5
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共 55 条
  • [1] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes
    Alonso, Concepcion
    Martinez de Marigorta, Eduardo
    Rubiales, Gloria
    Palacios, Francisco
    [J]. CHEMICAL REVIEWS, 2015, 115 (04) : 1847 - 1935
  • [2] A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid
    Andrews, Keith G.
    Faizova, Radmila
    Denton, Ross M.
    [J]. NATURE COMMUNICATIONS, 2017, 8
  • [3] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source
    Chu, Lingling
    Qing, Feng-Ling
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) : 1513 - 1522
  • [4] Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines
    Deng, Qiao-Hui
    Chen, Jia-Rong
    Wei, Qiang
    Zhao, Quan-Qing
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (17) : 3537 - 3540
  • [5] Pd-Catalyzed Transfer of Difluorocarbene
    Deng, Xiao-Yun
    Lin, Jin-Hong
    Xiao, Ji-Chang
    [J]. ORGANIC LETTERS, 2016, 18 (17) : 4384 - 4387
  • [6] Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation
    Deng, Xiao-Yun
    Lin, Jin-Hong
    Zheng, Jian
    Xiao, Ji-Chang
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (42) : 8805 - 8808
  • [7] Direct Nucleophilic Difluoromethylation of Carbonyl Compounds
    Deng, Zuyong
    Lin, Jin-Hong
    Cai, Ji
    Xiao, Ji-Chang
    [J]. ORGANIC LETTERS, 2016, 18 (13) : 3206 - 3209
  • [8] The first fluoroalkylation of amino acids and peptides in water utilizing the novel iodonium salt (CF3SO2)2NI(Ph)CH2CF3
    DesMarteau, DD
    Montanari, V
    [J]. CHEMICAL COMMUNICATIONS, 1998, (20) : 2241 - 2242
  • [9] Fe-Catalyzed insertion of fluoromethylcarbenes generated from sulfonium salts into X-H bonds (X = Si, C, P)
    Duan, Yaya
    Lin, Jin-Hong
    Xiao, Ji-Chang
    Gu, Yu-Cheng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10): : 1917 - 1920
  • [10] Difluoromethylcarbene for iron-catalyzed cyclopropanation
    Duan, Yaya
    Lin, Jin-Hong
    Xiao, Ji-Chang
    Gu, Yu-Cheng
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (27) : 3870 - 3873
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