Synthesis of (Z)-α-Trifluoromethyl Alkenyl Triflate: A Scaffold for Diverse Trifluoromethylated Species

被引:29
作者
Zhao, Yilong [1 ]
Zhou, Yuhan [1 ]
Liu, Juan [1 ]
Yang, Dongmei [1 ]
Tao, Liang [1 ]
Liu, Yang [1 ]
Dong, Xiaoliang [1 ]
Liu, Jianhui [2 ]
Qu, Jingping [1 ]
机构
[1] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Dalian Univ Technol, Sch Petr & Chem Engn, Panjin 124221, Peoples R China
基金
中国国家自然科学基金;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; CONTAINING INTERNAL ALKYNES; CROSS-COUPLING REACTION; ONE-POT SYNTHESIS; STEREOCONTROLLED SYNTHESIS; ASYMMETRIC-SYNTHESIS; PRACTICAL SYNTHESIS; EFFICIENT SYNTHESIS; VINYLBORONIC ACIDS; PALLADIUM;
D O I
10.1021/acs.joc.6b00855
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of (Z) selective a-trifluoromethyl alkenyl triflates is described. As an important fluorinated building block, it is utilized successfully for the synthesis of various trifluoromethyl derivatives such as diarylethylenes, enynes, alkynes, and benzofurans.
引用
收藏
页码:4797 / 4806
页数:10
相关论文
共 103 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] Stereocontrolled synthesis of retinoids functionalized at C-13 by Suzuki coupling reactions
    Alvarez, R
    Iglesias, B
    de Lera, AR
    [J]. TETRAHEDRON, 1999, 55 (48) : 13779 - 13790
  • [3] Catalytic Trifluoromethylation of Aryl- and Vinylboronic Acids by 2-Cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium Triflate
    Arimori, Sadayuki
    Shibata, Norio
    [J]. ORGANIC LETTERS, 2015, 17 (07) : 1632 - 1635
  • [4] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
    Begue, Jean-Pierre
    Bonnet-Delpon, Daniele
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 992 - 1012
  • [5] Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry
    Brisdon, AK
    Crossley, IR
    [J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2420 - 2421
  • [6] A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions
    Byrne, Peter A.
    Rajendran, Kamalraj V.
    Muldoon, Jimmy
    Gilheany, Declan G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (17) : 3531 - 3537
  • [7] The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates
    Cho, Eun Jin
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2011, 13 (24) : 6552 - 6555
  • [8] Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3
    Chu, Lingling
    Qing, Feng-Ling
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) : 7262 - +
  • [9] Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent
    Dubbaka, Srinivas Reddy
    Nizalapur, Shashidhar
    Atthunuri, Azmi Reddy
    Salla, Manohar
    Mathew, Thresen
    [J]. TETRAHEDRON, 2014, 70 (12) : 2118 - 2121
  • [10] Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction
    Gao, Jian-Rong
    Wu, Hao
    Xiang, Bin
    Yu, Wu-Bin
    Han, Liang
    Jia, Yi-Xia
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) : 2983 - 2986