Intermolecular tandem Pd-catalyzed cross-coupling [4+4] and [4+2] cycloadditions: A one-pot, five-component assembly of bicyclo[6.4.0]dodecanes

被引：53
|
作者：
Lee, PH [1 ]
Lee, K [1 ]
机构：
[1] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 21期
关键词：
cross-coupling; cycloaddition; indium; palladium; tandem reactions;
D O I：
10.1002/anie.200461957
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Starting from α-bromovinylarenes, propargyl bromides, and dienophiles, a novel intermolecular tandem Pd-catalyzed cross-coupling/[4+4] and [4+2] cycloaddition sequence provides bicyclo[6.4.0]dodecane derivatives by a rapid synthesis in one reaction vessel. Five components are assembled into one molecule in this process. EWG = electronwithdrawing group. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：3253 / 3256
页数：4
相关论文
共 49 条
  • [1] Intermolecular tandem Pd-catalyzed cross-coupling [4+4] and [4+2] cycloadditions: One-pot five-component assembly to bicyclo[6.4.0]dodecanes.
    Lee, PH
    Lee, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U342 - U342
  • [2] Acid-Catalyzed Pseudo Five-Component Annulation for a General One-Pot Synthesis of 2,4,6-Triaryl Pyrimidines
    Ding, Yuxin
    Ma, Renchao
    Hider, Robert C.
    Ma, Yongmin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) : 242 - 246
  • [3] A novel efficient four- and five-component, one-pot synthesis of 4-semicarbazonoalkyl-2-naphthols
    Foroughifar, Naser
    Mobinikhaledi, Akbar
    Moghanian, Hassan
    Ebrahimi, Sattar
    Fard, Mohammad Ali Bodaghi
    SYNLETT, 2008, (06) : 821 - 826
  • [4] Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines
    Wang, Zijuan
    Chen, Wenteng
    He, Chang
    Zhang, Guolin
    Yu, Yongping
    SYNTHESIS-STUTTGART, 2021, 53 (07): : 1356 - 1364
  • [5] Base-promoted one-pot three-component desulphurization cross-coupling access to 4-cyanoimidazole
    Wen, Jiangwei
    Zeng, Ting
    Yan, Kelu
    Zhao, Lulu
    Zhu, Shuyun
    Yang, Jianjing
    CHEMICAL COMMUNICATIONS, 2023, 59 (74) : 11077 - 11080
  • [6] Tandem one-pot synthesis of flavans by recyclable silica-HClO4 catalyzed Knoevenagel condensation and [4+2]-Diels-Alder cycloaddition
    Bharate, Sandip B.
    Mudududdla, Ramesh
    Bharate, Jaideep B.
    Battini, Narsaiah
    Battula, Satyanarayana
    Yadav, Rammohan R.
    Singh, Baldev
    Vishwakarma, Ram A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (26) : 5143 - 5150
  • [7] Guanidine hydrochloride catalyzed efficient one-pot pseudo five-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in water
    Noruzian, Fatemeh
    Olyaei, Abolfazl
    Hajinasiri, Rahimeh
    Sadeghpour, Mandieh
    SYNTHETIC COMMUNICATIONS, 2019, 49 (20) : 2717 - 2724
  • [8] All-catalytic, efficient, and asymmetric synthesis of α,ω-diheterofunctional reduced polypropionates via "one-pot" Zr-catalyzed asymmetric carboalumination -: Pd-catalyzed cross-coupling tandem process
    Novak, T
    Tan, Z
    Liang, B
    Negishi, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2838 - 2839
  • [9] Synthesis of Polycyclic Isoindoline Derivatives via Tandem Pd-Catalyzed Coupling, Propargyl-Allenyl Isomerization, [4+2] Cycloaddition and Aromatization Reaction
    Zhu, Shugao
    Cao, Jian
    Wu, Luling
    Huang, Xian
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10409 - 10415
  • [10] Consecutive Five-Component Ugi-4CR-CAL B-Catalyzed Aminolysis Sequence and Concatenation with Transition Metal Catalysis in a One-Pot Fashion to Substituted Triamides
    Gesse, Pascal
    Mueller, Thomas J. J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (11) : 2150 - 2157
12345