Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling

被引：66

作者：

Bach, T ^{[1
]}

Heuser, S ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 11期

关键词：

palladium; palladium compounds; catalysis; coupling reactions; thiazoles;

D O I：

10.1016/S0040-4039(00)00018-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The difunctional substrate 2,4-dibromothiazole 2 was transformed into the title compounds 1 by consecutive Pd(0)-catalyzed cross-coupling reactions. Aryl zinc reagents which were prepared by ortho-lithiation of compounds 3 and subsequent transmetalation were used as carbon nucleophiles in the first coupling reaction. By this means, an aryl substituent was attached to the 2-position (50-62% yield). A succeeding cross-coupling with arylboronic acids 4 occurred at the 4-position of the intermediate 4-bromothiazoles 5 (76-97% yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1707 / 1710

页数：4

共 17 条

[1]

Bach T, 1999, EUR J ORG CHEM, V1999, P2045

[2] Sequential Pd(0)-catalyzed reactions for the construction of multiple substituted furans.: A short synthesis of the F5 furan fatty acid [J].

Bach, T ;

Krüger, L .

TETRAHEDRON LETTERS, 1998, 39 (13) :1729-1732

[3] PREPARATION OF SALICYLALDEHYDES VIA ORTHO-LITHIO DERIVATIVES OF METHOXYMETHYL-PROTECTED PHENOLS [J].

CHRISTENSEN, H .

SYNTHETIC COMMUNICATIONS, 1975, 5 (01) :65-78

[4]

Gschwend H. W., 1979, ORG REACTIONS, P1

[5]

Klpffer W, 1977, ADV PHOTOCHEM, P311, DOI DOI 10.1002/9780470133408.CH5

[6]

Kruger L, 1998, J INFORM REC, V24, P289

[7]

Liebscher J., 1994, METHODEN ORG CHEM B, VE8b, P1

[8]

Lowe N. J., 1990, SUNSCREENS DEV EVALU

[9]

Negishi E, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P1

[10]

Nicolaou K. C., 1998, ANGEW CHEM, V110, P89

← 1 2 →