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.
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页码：6574 / 6582
页数：9
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