Reactivity of 4-phenylthiazoles in ruthenium catalyzed direct arylations

被引：3

作者：

Daher, Ahmad ^{[1
]}

Jacquemin, Denis ^{[2
]}

Guerchais, Veronique ^{[1
]}

Soule, Jean-Francois ^{[1
]}

Doucet, Henri ^{[1
]}

机构：

[1] Univ Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France

[2] Univ Nantes, CNRS, CEISAM UMR 6230, 2 Rue Houssiniere, F-44322 Nantes 03, France

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2019年 / 33卷 / 04期

关键词：

arylation; C-C bond formation; C-H bond activation; palladium; ruthenium; H BOND FUNCTIONALIZATION; HIGHLY EFFICIENT; CHIRAL SULFONES; ACTIVATION; HETEROARENES; CARBOXYLATE; COMPLEXES; PARAMETERS; THIAZOLES; MECHANISM;

D O I：

10.1002/aoc.4794

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The reactivity of the phenyl substituent of 4-phenylthiazoles in Ru-catalyzed direct arylation was studied. 4-Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5-position of 4-phenylthiazole enhances its reactivity, allowing the selective mono-arylation of the phenyl unit of 4-phenylthiazoles in moderate to high yields using 5 mol% of [Ru(p-cymene)Cl-2](2) catalyst precursor associated to KOPiv as base. These results reveal that the conformation and electronic properties of 4-phenylthiazoles are crucial to allow the formation of suitable intermediates in the course of the catalytic cycle. The reaction tolerated both electron-rich and electron-poor aryl bromides allowing the straightforward tuning of the electronic properties of the arylated 2-methyl-4-phenyl-5-arylthiazoles.

引用

页数：11

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