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Progress in Chemistry 2013, Vol. 25 Issue (07): 1149-1157 DOI: 10.7536/PC121152 Previous Articles   Next Articles

• Review •

Application of 1,1-Dibromo-2-Arylalkene in Cyclization Reaction

Zhang Wensheng1*, Li Wei1, Kuang Chunxiang2*   

  1. 1. School of Technology, Jiaozuo Teachers College, Jiaozuo 454001, China;
    2. Department of Chemistry, Tongji University, Shanghai 200092, China
  • Received: Revised: Online: Published:
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1,1-Dibromo-2-arylalkenes, a kind of important organic intermediates, which are easily prepared from aryl aldehydes by Corey and Fuchs' procedure, have been found wide applications in the synthesis of polysubstituted alkenes, (E)-arylvinyl bromides, arynes, 1,3-diynes, polyynes, 1-bromo-1-alkynes and ynamines. Due to the difference of reactive activity between (E)-Br and (Z)-Br, 1,1-dibromo-2-arylalkenes are fit for designing tandem reaction. In recent years, various fused ring compounds and heterocyclic compounds bearing potential biological activities and synthetic value including isocoumarin, indene, indole, isoindole, benzothiophene and benzofuran, etc. were synthesized through 1,1-dibromo-2-arylalkenes based on Stille reaction, Heck reaction, Suzuki-Miyaura reaction, Buchwald-Hartwig reaction, etc. involving the (E)-Br and cyclization between the (E)-Br and the active group at the para-position of the aryl ring. In this paper, the application of 1,1-dibromo-2-arylalkenes on cyclization reaction in the past decade is surveyed. Contents
1 Introduction
2 Synthesis of isocoumarin derivatives
3 Synthesis of indene derivatives
4 Synthesis of indole derivatives
5 Synthesis of isoindole derivatives
6 Synthesis of polycyclic heterocyclic compounds
7 Synthesis of benzothiophene and benzofuran derivatives
8 Synthesis of heterocyclic compounds containing two heteroatoms
9 Comments and outlook

Key words: 1,1-dibromo-2-arylalkene, metal catalysis, cross-coupling, cyclization reaction, tandem reaction

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