Aromatic Cations from Oxidative Carbon-Hydrogen Bond Cleavage in Bimolecular Carbon-Carbon Bond Forming Reactions

被引：59

作者：

Clausen, Dane J. ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 15期

基金：

美国国家卫生研究院;

关键词：

CROSS-COUPLING REACTIONS; STEREOSELECTIVE-SYNTHESIS; CHROMENE ACETALS; DDQ; ETHERS; CYCLIZATION; PRINS; ACTIVATION; CATALYSIS; ALDEHYDES;

D O I：

10.1021/jo301185h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chromenes and isochromenes react quickly with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form persistent aromatic oxocarbenium ions through oxidative carbon-hydrogen cleavage. This process is tolerant of electron-donating and electron-withdrawing groups on the benzene ring and additional substitution on the pyran ring. A variety of nucleophiles can be added to these cations to generate a diverse set of structures.

引用

页码：6574 / 6582

页数：9

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