Preparation of 2-Silicon-Substituted 1,3-Dienes and Their Diels-Alder/Cross-Coupling Reactions

被引：23

作者：

Pidaparthi, Ramakrishna R. ^{[1
]}

Junker, Christopher S. ^{[1
]}

Welker, Mark E. ^{[1
]}

Day, Cynthia S. ^{[1
]}

Wright, Marcus W. ^{[1
]}

机构：

[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

基金：

美国国家科学基金会;

关键词：

ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; SILICON; METATHESIS; COMPLEXES;

D O I：

10.1021/jo901919m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Triethoxysilyi-substituted 1,3-butadiene has been prepared in 30-g quantities from chloroprene via a simple synthetic procedure. Silatrane- and catechol-substituted analogues of this main group element substituted diene were then prepared on a 10-g scale by ligand exchange and characterized by X-ray crystallography in addition to standard spectroscopic techniques. 2-Dimethylphenylsilyl-1,3-butadiene has also been prepared from chloroprene on an 8-g scale. Diels-Alder reactions of these dienes are reported as well as subsequent TBAF-assisted/Pd-catalyzed Hiyama cross-coupling reactions of those Diels-Alder adducts Silicon-substituted cycloadducts and cross-coupled products were also characterized by NMR spectroscopy and, in two cases, by X-ray crystallography.

引用

页码：8290 / 8297

页数：8

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