Copper-Catalyzed Cross-Coupling of Bicyclobutanes with Triftosylhydrazone Leading to Skipped Dienes

被引:0
|
作者
Zhang, Xiaolong [1 ]
Tian, Tian [1 ]
Liao, Peiqiu [1 ]
Liu, Zhaohong [1 ]
Murali, Karunanidhi [1 ]
Bi, Xihe [1 ,2 ]
机构
[1] Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[2] Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
BENZYLATION; STRAIN;
D O I
10.1021/acs.orglett.4c04519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, we report a protocol for the synthesis of skipped dienes through the cross-coupling of bicyclo[1.1.0]butanes with trifluoromethyl triftosylhydrazones. The reaction is run using TpBr3Cu(NCMe) as a catalyst to give access to a library of trifluoromethylated skipped dienes (32 examples, <= 98% yield) with excellent E/Z selectivity under mild and operationally safe conditions. The presented methods proved to be compatible with various functionalized bicyclo[1.1.0]butanes and triftosylhydrazones.
引用
收藏
页码:2300 / 2304
页数:5
相关论文
共 50 条
  • [1] Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling
    Arlow, Sophie I.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4567 - 4572
  • [2] Copper-Catalyzed Cross-Coupling of Arylacetylenes with Bromodifluoroacetamides
    Hu, Guo-Qin
    Yao, Li-Wei
    Gui, Shu-Sheng
    Geng, Chuang
    Zhang, Wen-Yan
    Liu, Jing-Hui
    Zhao, Bin
    SYNLETT, 2022, 33 (06) : 594 - 598
  • [3] Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
    Hojoh, Kentaro
    Shido, Yoshinori
    Nagao, Kazunori
    Mori, Seiji
    Ohmiya, Hirohisa
    Sawamura, Masaya
    TETRAHEDRON, 2015, 71 (37) : 6519 - 6533
  • [4] Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones
    Das, Arindam
    Wang, Dong
    Belhomme, Marie-Charlotte
    Szabo, Kalman J.
    ORGANIC LETTERS, 2015, 17 (19) : 4754 - 4757
  • [5] Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides
    Kou, Mengting
    Wei, Ziqiang
    Li, Zhen
    Xu, Bin
    ORGANIC LETTERS, 2022, 24 (46) : 8514 - 8519
  • [6] Recent progress in copper-catalyzed cross-coupling reactions
    Deng, W
    Liu, L
    Guo, QX
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (02) : 150 - 165
  • [7] Copper-catalyzed cross-coupling of arenediazonium tetrafluoroborates with polyfluoroarenes
    Zhu, Xingyi
    Li, Feng
    Su, Weike
    TETRAHEDRON LETTERS, 2013, 54 (10) : 1285 - 1289
  • [8] Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
    Wang, Long
    Huang, He
    Priebbenow, Daniel L.
    Pan, Fang-Fang
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3478 - 3480
  • [9] Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates
    Wang, Gao
    Yu, Qing-Ying
    Chen, Shan-Yong
    Yu, Xiao-Qi
    TETRAHEDRON LETTERS, 2013, 54 (46) : 6230 - 6232
  • [10] Copper-catalyzed cross-coupling and carbonylative cross-coupling of organostannanes and organoboranes with hypervalent iodine compounds
    Kang, SK
    Yamaguchi, T
    Kim, TH
    Ho, PS
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26): : 9082 - 9083