An efficient route to benzene and phenol derivatives via ring-closing olefin metathesis

被引:21
作者
Yoshida, Kazuhiro [1 ]
Horiuchi, Shingo [1 ]
Iwadate, Noriyuki [1 ]
Kawagoe, Fumihiro [1 ]
Imamoto, Tsuneo [1 ]
机构
[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
关键词
annulations; metathesis; ring closure; ruthenium; tautomerism;
D O I
10.1055/s-2007-982548
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Without the formation of inseparable regioisomers, various substituted phenol derivatives 2 and benzene derivatives 4 were prepared through RCM-tautomerization and RCM-dehydration protocols. A new synthetic route to precursors 1 and 3 enabled efficient access to these aromatic compounds.
引用
收藏
页码:1561 / 1564
页数:4
相关论文
共 27 条
[1]  
BACKVALL JE, 1995, ORGANOMETALLICS, V14, P4242
[2]   Reaction between ruthenium(0) complexes and dihalo compounds. A new method for the synthesis of ruthenium olefin metathesis catalysts [J].
Belderrain, TR ;
Grubbs, RH .
ORGANOMETALLICS, 1997, 16 (18) :4001-4003
[3]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[4]   Synthesis of fused bicyclic imidazoles by ring-closing metathesis [J].
Chen, YZ ;
Dias, HVR ;
Lovely, CJ .
TETRAHEDRON LETTERS, 2003, 44 (07) :1379-1382
[5]   Ring-closing metathesis as a basis for the construction of aromatic compounds [J].
Donohoe, TJ ;
Orr, AJ ;
Bingham, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2664-2670
[6]   Sequential and cascade palladium catalysed cyclisation-anion capture-olefin metathesis [J].
Evans, P ;
Grigg, R ;
Ramzan, MI ;
Sridharan, V ;
York, M .
TETRAHEDRON LETTERS, 1999, 40 (15) :3021-3024
[7]   Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis [J].
Hoveyda, AH ;
Gillingham, DG ;
Van Veldhuizen, JJ ;
Kataoka, O ;
Garber, SB ;
Kingsbury, JS ;
Harrity, JPA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (01) :8-23
[8]   A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction [J].
Huang, KS ;
Wang, EC .
TETRAHEDRON LETTERS, 2001, 42 (35) :6155-6157
[9]   Ring-closing olefin metathesis of 2,2'-divinylbiphenyls: A novel and general approach to phenanthrenes [J].
Iuliano, A ;
Piccioli, P ;
Fabbri, D .
ORGANIC LETTERS, 2004, 6 (21) :3711-3714
[10]   SELECTIVE CODIMERIZATION OF ACETYLENES AND ALLYL HALIDES CATALYZED BY PALLADIUM COMPLEXES [J].
KANEDA, K ;
UCHIYAMA, T ;
FUJIWARA, Y ;
IMANAKA, T ;
TERANISHI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 44 (01) :55-63