On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions

被引：131

作者：

Benitez, Diego ^{[1
]}

Tkatchouk, Ekaterina ^{[1
]}

Gonzalez, Ana Z. ^{[2
]}

Goddard, William A., III ^{[1
]}

Toste, F. Dean ^{[2
]}

机构：

[1] CALTECH, Mat & Proc Simulat Ctr, Pasadena, CA 91125 USA

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

关键词：

DENSITY FUNCTIONALS; GOLD; CATALYSIS; REARRANGEMENT; COMPLEXES; PLATINUM;

D O I：

10.1021/ol9018002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is shown that [4 + 3] and [4 + 2] cycloaddition pathways are accessible In the Au(I) catalysis of allene-dienes. Seven-membered ring gold-stabilized carbenes, originating from the [4 + 3] cycloaddition process, are unstable and can rearrange via a 1,2-H or a 1,2-alkyl shift to yield six- and seven-membered products. Botti steric and electronic properties of the AuL+ catalyst affect the electronic structure of the intermediate gold-stabilized carbene and its subsequent reactivity.

引用

页码：4798 / 4801

页数：4

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