Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines

被引：19

作者：

Asano, Shigehiro ^{[1
]}

Kamioka, Seiji ^{[1
]}

Isobe, Yoshiaki ^{[1
]}

机构：

[1] Dainippon Sumitomo Pharma Co Ltd, Drug Res Div, Konohana Ku, Osaka 5540022, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 01期

关键词：

Suzuki-Miyaura cross-coupling reaction; 2-Heteroaryl pinacol boronates; 2-Chloropyrimidyl derivatives; 2-Heteroaryl pyrimidines; Pd(OAc)(2)/S-Phos; Lithium hydroxide; HETEROCYCLIC CARBENE LIGANDS; BORONIC ACIDS; ORGANOBORON COMPOUNDS; EFFICIENT SYNTHESIS; POTASSIUM ARYL; CHLORIDES; CATALYST; COMPLEXES; HALIDES; INHIBITORS;

D O I：

10.1016/j.tet.2011.10.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suzuki-Miyaura cross-coupling reaction with 2-heteroarylboronic acids is generally challenging due to these acids easy decomposition. To overcome this problem, we developed a coupling method that uses 2-heteroaryl pinacol boronates in the presence of 1.0 mol % Pd(OAc)(2) and 2.0 mol % S-Phos with 4 equiv amount of LiOH in dioxane and H2O at 80 degrees C for 30 min. This developed method allowed for the synthesis of a wide variety of 2-heteroaryl pyrimidines from 2-chloropyrimidyl derivatives in high yields, and is also useful in the preparation of various biaryl derivatives from heteroaryl chlorides. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：272 / 279

页数：8

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