Eliminative Deoxofluorination Using XtalFluor-E: A One-Step Synthesis of Monofluoroalkenes from Cyclohexanone Derivatives

被引:14
|
作者
Vandamme, Mathilde [1 ]
Paquin, Jean-Francois [1 ]
机构
[1] Univ Laval, Dept Chim, PROTEO, CGCC, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
IN-SITU ACTIVATION; CYCLODEHYDRATION AGENT; CARBOXYLIC-ACIDS; BENZYL ALCOHOLS; FLUORINATION; FLUOROALKENES; METATHESIS; OLEFINATION; FLUORIDES; EFFICIENT;
D O I
10.1021/acs.orglett.7b01581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The eliminative deoxofluorination of cyclohexanone derivatives using XtalFluor-E is described. The corresponding monofluoroalkenes are obtained in up to 79% yield. Notably, this one-step procedure occurs at room temperature using readily accessible and cost-effective reagents.
引用
收藏
页码:3604 / 3607
页数:4
相关论文
共 50 条
  • [1] Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E
    Gonay, Marie
    Batisse, Chloe
    Paquin, Jean-Francois
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15): : 10253 - 10260
  • [2] Synthesis of isocyanides through dehydration of formamides using XtalFluor-E
    Keita, Massaba
    Vandamme, Mathilde
    Mahe, Olivier
    Paquin, Jean-Francois
    [J]. TETRAHEDRON LETTERS, 2015, 56 (02) : 461 - 464
  • [3] Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E
    Keita, Massaba
    Vandamme, Mathilde
    Paquin, Jean-Francois
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (23): : 3758 - 3766
  • [4] One-Step Stereoselective Synthesis of Trisubstituted Monofluoroalkenes from 3,3,3-Trifluoropropionates
    Lecea, Mercedes
    Grassin, Adrien
    Ferreiro-Mederos, Leticia
    Choppin, Sabine
    Urbano, Antonio
    Carmen Carreno, M.
    Colobert, Francoise
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (21) : 4486 - 4489
  • [5] Novel One-Step Synthesis Process from Cyclohexanone to Caprolactam in Trifluoroacetic Acid
    Zhang, Jisong
    Lu, Yangcheng
    Wang, Kai
    Luo, Guangsheng
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2013, 52 (19) : 6377 - 6381
  • [6] A ONE-STEP SYNTHESIS OF THIOPHENE DERIVATIVES
    SAITO, K
    KAMBE, S
    [J]. SYNTHESIS-STUTTGART, 1982, (12): : 1056 - 1059
  • [7] XtalFluor-E: An Efficient Reagent for Synthesis of Oxazolines from Carboxylic Acids and O-Silylated Amino Alcohols
    Kumar, Vadiga Shanthi
    Gudise, Veera Babu
    Reddy, Eeda Koti
    Anwar, Shaik
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (10) : 2753 - 2760
  • [8] A convenient one-step synthesis of fluoroethylidene derivatives
    Chevrie, D
    Lequeux, T
    Demoute, JP
    Pazenok, S
    [J]. TETRAHEDRON LETTERS, 2003, 44 (44) : 8127 - 8130
  • [9] One-Step Synthesis of Janus Fluorographene Derivatives
    Kouloumpis, Antonios
    Chronopoulos, Demetrios D.
    Potsi, Georgia
    Pykal, Martin
    Vlcek, Jakub
    Scheibe, Magdalena
    Otyepka, Michal
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (29) : 6518 - 6524
  • [10] One-Step Synthesis of Phosphorylated Vinylacethylene Derivatives
    Brel, V. K.
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (11) : 2212 - 2218