Copper-catalyzed tandem trifluoromethylation-cyclization of olefinic carbonyls: synthesis of trifluoromethylated 2,3-dihydrofurans and 3,4-dihydropyrans

被引：31
作者：
Bai, Xiaohui [1 ]
Lv, Leiyang [1 ]
Li, Zhiping [1 ]
机构：
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 07期
基金：
美国国家科学基金会;
关键词：
CENTERED RADICAL-ADDITION; DICARBONYL-COMPOUNDS; CASCADE SYNTHESIS; FACILE SYNTHESIS; BOND FORMATION; ALKENES; DIHYDROFURANS; CONSTRUCTION; ALKYNES; FURANS;
D O I：
10.1039/c6qo00137h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed trifluoromethylation-cyclization of olefinic carbonyls was developed. With this method, a variety of 2,3-dihydrofuran and 3,4-dihydropyran derivatives containing a CF3 group were selectively obtained in moderate to good yields. This chemistry represents a rare example of direct construction of trifluoromethylated oxygen-containing heterocycles via the combination of radical trifluoromethylation with endo-type radical addition to carbonyls.
引用
收藏
页码：804 / 808
页数：5
相关论文
共 58 条
  • [1] N-Heterocyclic Carbene Catalysis as a Tool for Gaining Access to the 3,4-Dihydropyran-2-one Skeleton
    Albanese, Domenico C. M.
    Gaggero, Nicoletta
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (26) : 5631 - 5640
  • [2] Like (CO)4, Do (CS)4 and (CSe)4 Have a Triplet Ground State?
    Bao, Xiaoguang
    Hrovat, David A.
    Borden, Weston Thatcher
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (18) : 5687 - 5693
  • [3] KINETICS AND MECHANISM OF THE EXO CYCLIZATIONS OF OMEGA-FORMYLALKYL RADICALS
    BECKWITH, ALJ
    HAY, BP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2674 - 2681
  • [4] Cao P., 2013, CHEM-EUR J, V19, P14420
  • [5] Chemistry of acyl radicals
    Chatgilialoglu, C
    Crich, D
    Komatsu, M
    Ryu, I
    [J]. CHEMICAL REVIEWS, 1999, 99 (08) : 1991 - 2069
  • [6] Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans
    Cui, Xin
    Xu, Xue
    Wojtas, Lukasz
    Kim, Martin M.
    Zhang, X. Peter
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (49) : 19981 - 19984
  • [7] Radical cyclizations of acylgermanes. New reagent equivalents of the carbonyl radical acceptor synthon
    Curran, DP
    Diederichsen, U
    Palovich, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) : 4797 - 4804
  • [8] Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups
    Egami, Hiromichi
    Sodeoka, Mikiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) : 8294 - 8308
  • [9] Strategy and methodology development for the total synthesis of polyether ionophore antibiotics
    Faul, MM
    Huff, BE
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2407 - 2473
  • [10] Radicals from epoxides.: Intramolecular addition to aldehyde and ketone carbonyls
    Fernández-Mateos, A
    de la Nava, EM
    Coca, GP
    Silvo, AR
    González, RR
    [J]. ORGANIC LETTERS, 1999, 1 (04) : 607 - 609
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