Regioselective arylation on the γ-position of α,β-unsaturated carbonyl compounds with aryl bromides by palladium catalysis

被引:72
作者
Terao, Y [1 ]
Satoh, T [1 ]
Miura, M [1 ]
Nomura, M [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
arylation; enals; enones; palladium and compounds;
D O I
10.1016/S0040-4039(98)01275-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arylation of 2-substituted 2-alkenals and 3-substituted 2-cyclohexen- and 2-cyclopenten-1-ones can effectively and regioselectively proceed at their gamma-position by treatment with aryl bromides in the presence of a palladium catalyst and a base. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6203 / 6206
页数:4
相关论文
共 19 条
[1]   UNPRECEDENTED INTRA- AND INTERMOLECULAR PALLADIUM-CATALYZED COUPLING REACTIONS WITH METHYLENECYCLOPROPANE-TYPE TETRASUBSTITUTED ALKENES [J].
BRASE, S ;
DEMEIJERE, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (22) :2545-2547
[2]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[3]  
Dyker G, 1997, LIEBIGS ANN-RECL, P203
[4]   Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383
[5]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[6]  
HILLERS S, 1995, SYNLETT, P153
[7]   Palladium-catalyzed coupling reaction of 4-alkylnitrobenzenes with aryl bromides at their benzylic position [J].
Inoh, J ;
Satoh, T ;
Pivsa-Art, S ;
Miura, M ;
Nomura, M .
TETRAHEDRON LETTERS, 1998, 39 (26) :4673-4676
[8]   PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION OF FUNCTIONALLY-SUBSTITUTED CYCLOALKENES BY ARYL IODIDES [J].
LAROCK, RC ;
YUM, EK ;
YANG, HS .
TETRAHEDRON, 1994, 50 (02) :305-321
[9]   PALLADIUM-CATALYZED ARYLATION OF ALLYLIC ALCOHOLS WITH ARYL HALIDES [J].
MELPOLDER, JB ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :265-272
[10]   NOVEL SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES BY THE PALLADIUM-CATALYZED ARYLATION OF KETENES WITH AROYL CHLORIDES OR THE DECARBONYLATIVE CROSS-CONDENSATION OF ACYL HALIDES [J].
MITSUDO, T ;
KADOKURA, M ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3186-3192