MECHANISTIC STUDIES OF THE SUZUKI CROSS-COUPLING REACTION

被引：229

作者：

SMITH, GB

DEZENY, GC

HUGHES, DL

KING, AO

VERHOEVEN, TR

机构：

[1] Department of Process Research, Merck Research Laboratories, Division of Merck & Co., Inc., Rahway, New Jersey 07065-0900

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The key step in the synthesis of the drug substance losartan is a palladium-catalyzed cross-coupling reaction of an aryl bromide and a boronic acid. The reaction scheme was defined in kinetic studies using HPLC, and computer simulation served to depict the time dependence of the concentrations of palladium species, which were not observed experimentally. Two catalyst poisons were identified and characterized. One was an isomeric impurity of the aryl bromide; the other formed in the reaction mixture upon hydrolysis of the boronic acid and two of its impurities.

引用

页码：8151 / 8156

页数：6

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