Palladium-catalyzed carbonylative coupling of iodobenzene and 2-methyl-3-butyn-2-ol under biphasic conditions: Formation of furanones

被引：16

作者：

Kiji, J

Okano, T

Kimura, H

Saiki, K

机构：

[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 680, Japan

[2] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 658, Japan

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1998年 / 130卷 / 1-2期

关键词：

D O I：

10.1016/S1381-1169(97)00202-1

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Carbonylative coupling of iodobenzene and 2-methyl-3-butyn-2-ol (4) in aqueous NaOH/benzene was carried out by using Pd(OAc)(2)/Ph3P/Bu4PBr (A) and Pd(OAc)(2)/Ph2P(m-C6H4SO3Na) (B) as catalyst. In sharp contrast with a homogeneous Et3N solution, this biphasic solvent system gives 3-isopropylidene-5-phenyl-2(2H)-furanone (1) in a moderate yield. The other carbonylated products are 2,2-dimethyl-5-phenyl-3(2H)-furanone (2) and benzoic acid. The formation of 1 is explained by the following sequential reactions; carbonylative coupling of iodobenzene with 4 to form 4-hydroxy-4methyl-1 -phenyl-2-pentyn-1-one (6), hydrogenolysis of 6 to 4-methyl-1-phenyl-2,3-pentadien-1-one (8) and its cyclocarbonylation to 1. Catalyst A gives 1 in a higher yield than B. (C) 1998 Elsevier Science B.V.

引用

页码：95 / 100

页数：6

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