Palladium-catalyzed annulation reaction of o-bromobenzaldehydes with carbonyl compounds to produce naphthol and/or naphthalene derivatives

被引:34
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
annulation; arylation; carbonyl compounds; palladium and compounds;
D O I
10.1016/S0040-4020(00)00043-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
o-Bromobenzaldehydes undergo annulation with 1,3-diaryl-2-propanones in the presence of a palladium catalyst to give the corresponding 1,3-diaryl-2-naphthols in fair to good yields. From the reaction of the aldehydes with 2-substituted 2-alkenals are formed 2,4-disubstituted 1-naphthols and/or 1,3-disubstituted naphthalenes accompanied by decarbonylation. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1315 / 1320
页数:6
相关论文
共 34 条
[1]   Asymmetric arylation of ketone enolates [J].
Ahman, J ;
Wolfe, JP ;
Troutman, MV ;
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919
[2]   STANDARD CHEMICAL THERMODYNAMIC PROPERTIES OF ALKYLNAPHTHALENE ISOMER GROUPS [J].
ALBERTY, RA ;
BLOOMSTEIN, TM .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1985, 14 (03) :821-837
[3]  
Diederich F., 1997, METAL CATALYZED CROS
[4]   COMPETITIVE DIENONE-PHENOL TYPE REARRANGEMENTS FOR THE REGIOSELECTIVE PREPARATION OF 2,4-DISUBSTITUTED-NAPHTH-1-OLS [J].
DODGE, JA ;
CHAMBERLIN, AR .
TETRAHEDRON LETTERS, 1988, 29 (38) :4827-4830
[5]   Annulated ring-systems by Domino-Heck-Aldol-condensation and Domino-Heck-Michael-addition processes [J].
Dyker, G ;
Grundt, P .
TETRAHEDRON LETTERS, 1996, 37 (05) :619-622
[6]   Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes [J].
Gevorgyan, V ;
Quan, LG ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1999, 40 (21) :4089-4092
[7]   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
[8]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[9]  
HUSIGEN R, 1969, CHEM BER, V102, P3405
[10]   Simple, highly active palladium catalysts for ketone and malonate arylation: Dissecting the importance of chelation and steric hindrance [J].
Kawatsura, M ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (07) :1473-1478