Synthesis of Substituted Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Metathesis

被引:1
作者
Yoshida, Kazuhiro [1 ]
Imamoto, Tsuneo [1 ]
Yanagisawa, Akira [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan
关键词
aromatic compound; aromatization; carbon-carbon bond formation; elimination; isomerization; ring-closing metathesis; ruthenium catalyst; tautomerization; N-HETEROCYCLIC CARBENE; OLEFIN METATHESIS; ENYNE METATHESIS; CLAISEN REARRANGEMENT; 2+2+2 CYCLOADDITION; PHENOL DERIVATIVES; EFFICIENT; BENZENE; ISOMERIZATION; COMPLEXES;
D O I
10.5059/yukigoseikyokaishi.67.876
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The demand for functionalized aromatic compounds is growing rapidly in many research fields. Therefore, the efficient synthesis of desired aromatic compounds is a critical issue in organic synthesis. In this account, we describe new synthetic approaches to versatile aromatic compounds, such as phenols, benzenes, 3-hydroxypyridines, and styrenes, by ring-closing olefin metathesis (RCM)/aromatization and ring-closing enyne metathesis (RCEM)/aromatization of acyclic precursors. The advantages in terms of simplicity, flexibility, and avoidance of the formation of regioisomers are proof of the versatility of this method for the synthesis of aromatic compounds.
引用
收藏
页码:876 / 888
页数:13
相关论文
共 132 条
  • [1] A practical protocol for the synthesis of 3-hydroxy-4,5-disubstituted pyridine derivatives from acyclic compounds
    Anastasia, L
    Anastasia, M
    Allevi, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (19): : 2404 - 2408
  • [2] RHODIUM-CATALYZED ISOMERIZATION OF SOME UNSATURATED ORGANIC SUBSTRATES
    ANDRIEUX, J
    BARTON, DHR
    PATIN, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (04): : 359 - 363
  • [3] Preparation of N-sulfonyl-2-quinolinone using ring-closing metathesis(RCM)
    Arisawa, M
    Theeraladanon, C
    Nishida, A
    [J]. HETEROCYCLES, 2005, 66 : 683 - 688
  • [4] Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis
    Arisawa, M
    Terada, Y
    Nakagawa, M
    Nishida, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) : 4732 - 4734
  • [5] Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene-ene metathesis and ene-enol ether metathesis
    Arisawa, M
    Theeraladanon, C
    Nishida, A
    Nakagawa, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (45) : 8029 - 8033
  • [6] Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis
    Arisawa, Mitsuhiro
    Nishida, Atsushi
    Nakagawa, Masako
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) : 5109 - 5121
  • [7] Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
    Arisawa, Mitsuhiro
    Terada, Yukiyoshi
    Takahashi, Kazuyuki
    Nakagawa, Masako
    Nishida, Atsushi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) : 4255 - 4261
  • [9] Astruc D., 2002, MODERN ARENE CHEM
  • [10] BACKVALL JE, 1995, ORGANOMETALLICS, V14, P4242