Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls

被引：72

作者：

Chernyak, Natalia ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 7-8期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

alkynes; annulations; arylation; C-H activation; palladium; C-H ACTIVATION; PROTON-ABSTRACTION MECHANISM; ORTHO-ARYLATION; INTRAMOLECULAR HYDROARYLATION; DOMINO REACTIONS; TRIPLE BONDS; ALKYNES; ARYL; FUNCTIONALIZATION; SP(2);

D O I：

10.1002/adsc.200800765

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The direct palladium-catalyzed intramolecular hydroarylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorporated in this transformation, allowed for the efficient synthesis of fully substituted fluorenes 12. These cyclizations proceed more rapidly with electron-deficient benzene rings which, in combination with a substantial isotope effect observed, strongly supports a C-H activation mechanism for the key annulation step.

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页码：1101 / 1114

页数：14

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