Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-Coupling Reactions with Electron-Rich Olefins

被引：46

作者：

Gogsig, Thomas M. ^{[1
,2
]}

Lindhardt, Anders T. ^{[1
,2
]}

Dekhane, Mouloud ^{[3
]}

Grouleff, Julie ^{[1
,2
]}

Skrydstrup, Troels ^{[1
,2
]}

机构：

[1] Aarhus Univ, Ctr Insoluble Prot Struct inSPIN, Dept Chem, DK-8000 Aarhus, Denmark

[2] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus, Denmark

[3] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 24期

基金：

新加坡国家研究基金会;

关键词：

aryl tosylates; C-C coupling; Mizoroki-Heck coupling; heterocycles; palladium; PALLADIUM-CATALYZED ARYLATION; HYDROXYALKYL VINYL ETHERS; ARYL HALIDES; ASYMMETRIC HYDROGENATION; CONVENIENT SYNTHESIS; ARYLBORONIC ACIDS; MILD CONDITIONS; SUZUKI; CHLORIDES; BROMIDES;

D O I：

10.1002/chem.200900313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.

引用

页码：5950 / 5955

页数：6

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