Synthesis of Sulfur-Containing Heterocycles through Oxidative Carbon-Hydrogen Bond Functionalization

被引：61

作者：

Cui, Yubo ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 07期

基金：

美国国家卫生研究院;

关键词：

C-H ACTIVATION; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; DIASTEREOSELECTIVE SYNTHESIS; CONFORMATIONAL-ANALYSIS; PUMMERER REACTION; ORGANIC-SYNTHESIS; CARBENIUM IONS; PRINS; DERIVATIVES;

D O I：

10.1021/ol3002877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form alpha,beta-unsaturated thiocarbenium ions through oxidative carbon-hydrogen bond cleavage. These electrophiles couple with appended pi-nucleophiles to yield sulfur-containing heterocycles through carbon-carbon bond formation. Several nucleophiles are compatible with the procedure, and the reactions generally proceed through readily predictable transition states.

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页码：1720 / 1723

页数：4

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