Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides

被引：25
作者：
Hamel, Jean-Denys [1 ]
Hayashi, Tatsuru [1 ]
Cloutier, Melissa [1 ]
Savoie, Paul R. [1 ]
Thibeault, Olivier [1 ]
Beaudoin, Meggan [1 ]
Paquin, Jean-Francois [1 ]
机构：
[1] Univ Laval, CCVC, PROTEO, Dept Chim, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 46期
基金：
加拿大自然科学与工程研究理事会;
关键词：
SPECTRUM DEOXOFLUORINATING AGENT; ENHANCED THERMAL-STABILITY; C-F BOND; MEDICINAL CHEMISTRY; BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE; ALPHA; ALPHA-DIFLUOROARYLACETIC ACIDS; DECARBOXYLATIVE ALKYNYLATION; ALKYNES; FLUORINE; COMPLEXES;
D O I：
10.1039/c7ob02406a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.
引用
收藏
页码：9830 / 9836
页数：7
相关论文
共 86 条
  • [1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks
    Ahrens, Theresia
    Kohlmann, Johannes
    Ahrens, Mike
    Braun, Thomas
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 931 - 972
  • [2] Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents
    Beaulieu, Francis
    Beauregard, Louis-Philippe
    Courchesne, Gabriel
    Couturier, Michel
    LaFlamme, Francois
    L'Heureux, Alexandre
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 5050 - 5053
  • [3] Organic fluorine compounds: a great opportunity for enhanced materials properties
    Berger, Ricarda
    Resnati, Giuseppe
    Metrangolo, Pierangelo
    Weber, Edwin
    Hulliger, Juerg
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3496 - 3508
  • [4] BILDSTEIN S, 1995, TETRAHEDRON LETT, V36, P5007
  • [5] Boswell G.A., 1974, ORG REACT, V21, P1
  • [6] Box JM, 1997, SYNLETT, P571
  • [7] 3,3-DIFLUOROCHLORAMBUCIL
    BUSS, CW
    COE, PL
    TATLOW, JC
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1986, 34 (01) : 83 - 104
  • [8] Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis
    Campbell, Michael G.
    Ritter, Tobias
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 612 - 633
  • [9] Monofluorination of Organic Compounds: 10 Years of Innovation
    Champagne, Pier Alexandre
    Desroches, Justine
    Hamel, Jean-Denys
    Vandamme, Mathilde
    Paquin, Jean-Francois
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9073 - 9174
  • [10] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
    Charpentier, Julie
    Frueh, Natalja
    Togni, Antonio
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682
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