Palladium-Catalyzed Intermolecular Aryldifluoroalkylation of Alkynes

被引：98
|
作者：
He, Yu-Tao [1 ]
Wang, Qiang [1 ]
Li, Lian-Hua [1 ]
Liu, Xue-Yuan [1 ]
Xu, Peng-Fei [1 ]
Liang, Yong-Min [1 ,2 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 21期
关键词：
ARYL BORONIC ACIDS; MEDIATED RADICAL ARYLDIFLUOROACETYLATION; OXIDATIVE TRIFLUOROMETHYLATION; ETHYL BROMODIFLUOROACETATE; UNACTIVATED ALKENES; BOND-FORMATION; DIFLUOROMETHYLATION; HYDROTRIFLUOROMETHYLATION; DIFLUOROACETYLATION; DIFLUOROALKYLATION;
D O I：
10.1021/acs.orglett.5b02512
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed aryldifluoroalkylation of alkynes with ethyl difluoroiodoacetate and arylboronic acids as reaction partners is described. The alkyne difunctionalization process provides various aryldifluoroalkylated products in one pot under mild reaction conditions. A wide range of alkynes and diverse arylboronic acids are compatible with these reaction conditions. High reaction efficiency and broad substrate scope are the notable features of this transformation. Preliminary mechanistic investigations indicate that a difluoroalkyl radical addition pathway is involved in this transformation.
引用
收藏
页码：5188 / 5191
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Intermolecular Aryliodination of Internal Alkynes
    Lee, Yong Ho
    Morandi, Bill
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6444 - 6448
  • [2] Palladium-Catalyzed Intermolecular Addition of Formamides to Alkynes
    Fujihara, Tetsuaki
    Katafuchi, Yuko
    Iwai, Tomohiro
    Terao, Jun
    Tsuji, Yasushi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 2094 - 2098
  • [3] Palladium-Catalyzed Intermolecular Addition of Formamides to Alkynes
    Tsuji, Yasushi
    Katafuchi, Yuko
    Iwai, Tomohiro
    Terao, Jun
    Fujihara, Tetsuaki
    [J]. SYNLETT, 2010, (08) : A41 - A42
  • [4] Palladium-Catalyzed Remote Aryldifluoroalkylation of Alkenyl Aldehydes
    Nie, Xingliang
    Cheng, Cungui
    Zhu, Gangguo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (07) : 1898 - 1902
  • [5] Palladium-catalyzed cyclotrimerization of alkynes
    Zhou, L
    Jiang, HF
    Huang, JM
    Tang, JY
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (01) : 1 - 8
  • [6] PALLADIUM-CATALYZED HYDROCARBOXYLATION OF ALKYNES
    ZARGARIAN, D
    ALPER, H
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 319 - INOR
  • [7] Palladium-catalyzed addition of tetragermetanes to alkynes
    Mochida, K
    Hirahue, K
    Suzuki, K
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (05) : 1023 - 1028
  • [8] Palladium-catalyzed addition of alkynes to cyclopropenes
    Yin, JD
    Chisholm, JD
    [J]. CHEMICAL COMMUNICATIONS, 2006, (06) : 632 - 634
  • [9] Palladium-catalyzed additions of terminal alkynes to acceptor alkynes
    Trost, BM
    Sorum, MT
    Chan, C
    Harms, AE
    Ruhter, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) : 698 - 708
  • [10] Palladium-Catalyzed Aminocarbonylation of Alkynes to Succinimides
    Liu, Huizhen
    Lau, Genevieve P. S.
    Dyson, Paul J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 386 - 391
12345