Palladium-catalyzed enyne-yne [4+2] benzannulation as a new and general approach to polysubstituted benzenes

被引:101
作者
Gevorgyan, V [1 ]
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
enynes; diynes; alkynes; palladium; cycloaddition; benzene;
D O I
10.1016/S0022-328X(98)01061-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, alpha- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:232 / 247
页数:16
相关论文
共 80 条
[1]   Diastereoselective cyclopropanation of simple alkenes by 2-phenyl- and 2-ferrocenylalkenyl Fischer carbene complexes of chromium [J].
Barluenga, J ;
FernandezAcebes, A ;
Trabanco, AA ;
Florez, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) :7591-7592
[2]   A NEW APPROACH TO THE CONSTRUCTION OF BIPHENYLENES BY THE COBALT-CATALYZED COCYCLIZATION OF ORTHO-DIETHYNYLBENZENES WITH ALKYNES - APPLICATION TO AN ITERATIVE APPROACH TO [3]PHENYLENE, THE 1ST MEMBER OF A NOVEL CLASS OF BENZOCYCLOBUTADIENOID HYDROCARBONS [J].
BERRIS, BC ;
HOVAKEEMIAN, GH ;
LAI, YH ;
MESTDAGH, H ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5670-5687
[3]  
BERTHELOT MC, 1866, R ACAD SCI, V62, P905
[4]  
BORRINI A, 1985, J MOL CATAL, V30, P181, DOI 10.1016/0304-5102(85)80026-2
[5]  
Boundy R.H, 1952, STYRENE ITS POLYM CO
[6]  
BOYER RF, 1970, ENCY POLYM SCI TECHN, V13
[7]   2,2-BIS(TRIFLUOROMETHYL)ETHYLENE-1,1-DICARBONITRILE AND STYRENES - A DICHOTOMY OF CYCLOADDITION PATHWAYS [J].
BRUCKNER, R ;
HUISGEN, R ;
SCHMID, J .
TETRAHEDRON LETTERS, 1990, 31 (49) :7129-7132
[8]   Strained cyclic cumulene intermediates in Diels-Alder cycloadditions of enynes and diynes [J].
Burrell, RC ;
Daoust, KJ ;
Bradley, AZ ;
DiRico, KJ ;
Johnson, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4218-4219
[9]   A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].
Catellani, M ;
Frignani, F ;
Rangoni, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122
[10]   STEREOSELECTIVE AND REGIOSELECTIVE METAL SALT-CATALYZED ALKYNYLATION OF 1,2-EPOXIDES [J].
CHINI, M ;
CROTTI, P ;
FAVERO, L ;
MACCHIA, F .
TETRAHEDRON LETTERS, 1991, 32 (45) :6617-6620