Copper-Catalyzed Bromodifluoroacetylative Cyclization of Enynes

被引:26
作者
Zhu, Shaoqun [1 ]
Yang, Haibo [1 ]
Jiang, Along [1 ]
Zhou, Bing [1 ]
Han, Ying [1 ]
Yan, Chaoguo [1 ]
Shi, Yaocheng [1 ]
Hou, Hong [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225009, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
ETHYL BROMODIFLUOROACETATE; DIFLUOROALKYLATION; CONSTRUCTION; FLUORINE; ALKYNES; FLUOROALKYLATIONS; PHOSPHONATES; ELUCIDATION; BONDS; ACIDS;
D O I
10.1021/acs.joc.0c02114
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed bromodifluoroacetylative cyclization reaction is described. The treatment of bromodifluoroacete derivatives by CuI and B(2)Pin(2) enables difluoroalkyl radical generation and triggers the radical addition/cyclization/bromination sequences. Bromodifluoroacetyl-derived ester, amide, and ketone were compatible and gave various vinyl C-Br bonds containing functionalized heterocycles in good yields.
引用
收藏
页码:15667 / 15675
页数:9
相关论文
共 69 条
  • [1] Direct Access to α,α-Difluoroacylated Arenes by Palladium-Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives
    Andersen, Thomas L.
    Frederiksen, Mette W.
    Domino, Katrine
    Skrydstrup, Troels
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) : 10396 - 10400
  • [2] [Anonymous], 2006, Organofluorine Chemistry
  • [3] Fleming-Tamao oxidation and masked hydroxyl functionality: Total synthesis of (+)-pramanicin and structural elucidation of the antifungal natural product (-)-pramanicin
    Barrett, AGM
    Head, J
    Smith, ML
    Stock, NS
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 6005 - 6018
  • [4] The chemistry and biology of guanidine natural products
    Berlinck, Roberto G. S.
    Romminger, Stelamar
    [J]. NATURAL PRODUCT REPORTS, 2016, 33 (03) : 456 - 490
  • [5] A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with mechanisms distinct from Bortezomib
    Chauhan, D
    Catley, L
    Li, GL
    Podar, K
    Hideshima, T
    Velankar, M
    Mitsiades, C
    Mitsiades, N
    Yasui, H
    Letai, A
    Ovaa, H
    Berkers, C
    Nicholson, B
    Chao, TH
    Neuteboom, STC
    Richardson, P
    Palladino, MA
    Anderson, KC
    [J]. CANCER CELL, 2005, 8 (05) : 407 - 419
  • [6] Nickel-Catalyzed Site-Selective C-H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-Position
    Chen, Hao
    Li, Pinhua
    Wang, Min
    Wang, Lei
    [J]. ORGANIC LETTERS, 2016, 18 (19) : 4794 - 4797
  • [7] Cobalt-Catalyzed Three-Component Difluoroalkylation-Peroxidation of Alkenes
    Chen, Yuanjin
    Li, Liangkui
    Ma, Yangyang
    Li, Zhiping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09) : 5328 - 5338
  • [8] Corey EJ, 1999, CHEM PHARM BULL, V47, P1
  • [9] S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles
    Deng, Shuilin
    Chen, Haohua
    Ma, Xingxing
    Zhou, Yao
    Yang, Kai
    Lan, Yu
    Song, Qiuling
    [J]. CHEMICAL SCIENCE, 2019, 10 (28) : 6828 - 6833
  • [10] Elucidation of reaction process through β-halogen elimination in CuCN-mediated cyanation of (E)-1-bromo-2-iodoalkene
    Endo, Naoki
    Kanaura, Mao
    Iwasawa, Tetsuo
    [J]. TETRAHEDRON LETTERS, 2016, 57 (04) : 483 - 486