Palladium-Catalyzed Highly Regioselective [3+2] Cycloaddition Reactions of Alkylidenecyclopropa[b]naphthalenes with Alkenes or Alkynes: An Efficient Synthesis of 1(3)-Alkylidene-2,3-dihydro-1H-benzo[f]indenes and 1-Alkylidene-1H-benzo[f]indenes

被引:23
|
作者
Chen, Wanli [2 ]
Cao, Jian [1 ]
Huang, Xian [1 ,3 ]
机构
[1] Zhejiang Univ Technol, Ctr Anal & Measurement, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/ol8023083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first palladium-catalyzed highly regioselective [3 + 2] cycloaddition reactions of alkylidenecyclopropa[b]naphthalenes 1 with alkenes or alkynes is presented, providing an efficient method for the synthesis of 1(3)-alkylidene-2,3-dihydro-1H-benzo[f]indenes or 1-alkylidene-1H-benzo[f]indenes under mild conditions.
引用
收藏
页码:5537 / 5540
页数:4
相关论文
共 50 条
  • [1] SYNTHESIS OF DIHYDRO-1H-INDENES VIA A FORMAL 3+2 CYCLOADDITION
    ANGLE, SR
    ARNAIZ, DO
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 112 - ORGN
  • [2] PALLADIUM-CATALYZED BORYLATION OF ARYL IODIDES WITH 2,3-DIHYDRO-1H-BENZO [d] [1,3,2]DIAZABOROLES
    Murata, Mild
    Hirai, Nobuyoshi
    Okuyama, Michihiro
    Namikoshi, Takeshi
    Watanabe, Shinji
    HETEROCYCLES, 2014, 88 (01) : 193 - 199
  • [3] 2-Benzylidene-2,3-dihydro-1H-benzo[f]-chromen-1-one
    Marx, A.
    Manivannan, V.
    Suresh, R.
    Kanagam, Charles Christopher
    Buyukgungor, Orhan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4383 - U4019
  • [4] Samarium diiodide catalyzed synthesis of 2,3-dihydro-1H-benzo[b][1,4]-diazepine derivatives
    Luo, YQ
    Xu, F
    Han, XY
    Shen, Q
    CHINESE JOURNAL OF CHEMISTRY, 2005, 23 (10) : 1417 - 1420
  • [5] In(OTf)3-Catalyzed Synthesis of 2,3-Dihydro-1H-benzo[e]indoles and 2,3-Dihydrobenzofurans via [3+2] Annulation
    Liu, Shuxuan
    Zang, Yu
    Huang, Hai
    Sun, Jianwei
    ORGANIC LETTERS, 2020, 22 (21) : 8219 - 8223
  • [6] Crystal structure of 3-[4-(benzyloxy)phenyl]-2,3-dihydro-1H-benzo[f]chromen-1-one
    Vasanthi, R.
    Jonathan, D. Reuben
    Ezhilarasi, K. S.
    Sathya, S.
    Usha, G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O1116 - +
  • [7] Synthesis of (±)-cis-1-Aryl-3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carbonitriles and (±)-trans-4-Aryl-2-oxo-3,4-dihydro-2H-benzo[h]chromene-3-carbonitriles
    Mkaouar, Kamar
    Iriepa, Isabel
    Diez-Iriepa, Daniel
    Marco-Contelles, Jose
    Ismaili, Lhassane
    Chabchoub, Fakher
    CHEMISTRYSELECT, 2019, 4 (44): : 12902 - 12905
  • [8] Synthesis of 2,3-Dihydro-1H-benzo[b][1,4] diazepines with Aromatic Diamines and Acetonedicarboxylic Acid
    Song, Juhyun
    ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (16) : 5045 - 5048
  • [9] A Convenient Domino Synthesis of 4,9-Diphenyl-2,3-dihydro-1H-benzo[f]isoindole Derivatives
    Hu, Yi-min
    Lin, Xian-gang
    Zhu, Tao
    Wan, Jing
    Sun, Yong-jie
    Zhao, Quan-sheng
    Yu, Tao
    SYNTHESIS-STUTTGART, 2010, (20): : 3467 - 3473
  • [10] Palladium-Catalyzed [3+2] Cycloaddition Reaction of (Diarylmethylene)-cyclopropa[b]naphthalenes with Arynes: An Efficient Synthesis of 11-(Diarylmethylene)-11H-benzo[b]fluorenes
    Lin, Ying
    Wu, Luling
    Huang, Xian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) : 2993 - 3000