Palladium-catalyzed aromatization of β-bromovinyl aldehydes with alkenes

被引：38

作者：

Cho, CS ^{[1
]}

Patel, DB

Shim, SC

机构：

[1] Kyungpook Natl Univ, Dept Appl Chem, Taejon 702701, South Korea

[2] Kyungpook Natl Univ, Res Inst Ind Technol, Taejon 702701, South Korea

来源：

TETRAHEDRON | 2005年 / 61卷 / 40期

基金：

新加坡国家研究基金会;

关键词：

alkenes; aromatization; beta-bromovinyl aldehydes; Heck-Aldol reaction; palladium catalyst;

D O I：

10.1016/j.tet.2005.08.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Bromovinyl aldehydes, which are readily available from ketones and PBr3/DMF/CHCl3, are aromatized with suitably electron withdrawing group substituted alkenes in THF at 125 degrees C in the presence of a catalytic amount of a palladium catalyst along with a base. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：9490 / 9494

页数：5

共 28 条

[1]

AYED TB, 1995, SYNTHETIC COMMUN, V25, P3813

[2] A NOVEL ROUTE TO ISOANNULATED HETEROAROMATIC-COMPOUNDS .2. THE DIPOLE ROUTE TO FURO/THIENO PYRROLES AND ALPHA-PYRIDONES, AND THEIR BENZO DERIVATIVES [J].

BUSSENIUS, J ;

LABER, N ;

MULLER, T ;

EBERBACH, W .

CHEMISCHE BERICHTE, 1994, 127 (01) :247-259

[3]

Cho CS, 2002, J CHEM RES-S, P550

[4] Synthesis of 3-phenoxy-1,3-dihydro-1-isobenzofuranones by palladium-catalyzed carbonylative cyclization of 2-bromobenzaldehyde with phenols [J].

Cho, CS ;

Baek, DY ;

Shim, SC .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (04) :1101-1104

[5] Palladium-catalyzed synthesis of β-lactams via carbonylative cycloaddition of benzyl and allyl halides with imines [J].

Cho, CS ;

Jiang, LH ;

Shim, SC .

SYNTHETIC COMMUNICATIONS, 1999, 29 (15) :2695-2703

[6]

Cho CS, 2004, B KOREAN CHEM SOC, V25, P441

[7] Palladium-catalyzed tandem Heck and aldol reactions between 2-bromobenzaldehydes and functionalized alkenes leading to naphthalenes [J].

Cho, CS ;

Lim, DK ;

Zhang, JQ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2004, 45 (29) :5653-5656

[8] Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines [J].

Cho, CS ;

Lim, DK ;

Heo, NH ;

Kim, TJ ;

Shim, SC .

CHEMICAL COMMUNICATIONS, 2004, (01) :104-105

[9] Synthesis of isoindolinones via carbonylative cyclisation of 2-(2-bromophenyl)-2-oxazolines by a bimetallic palladium-nickel catalyst system [J].

Cho, CS ;

Lee, JW ;

Lee, DY ;

Shim, SC ;

Kim, TJ .

CHEMICAL COMMUNICATIONS, 1996, (18) :2115-2116

[10] Palladium-catalyzed diastereoselective synthesis of isoindolinones [J].

Cho, CS ;

Chu, DY ;

Lee, DY ;

Shim, SC ;

Kim, TJ ;

Lim, WT ;

Heo, NH .

SYNTHETIC COMMUNICATIONS, 1997, 27 (23) :4141-4158

← 1 2 3 →