Substituent Effect on the Formation and Reactivity of Platinum Carbenoids

被引：26

作者：

Cho, Eun Jin ^{[2
]}

Lee, Daesung ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 17期

关键词：

alkynes; carbenoids; cyclopropanes; platinum; substituent effects;

D O I：

10.1002/adsc.200800544

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A propargylic ester containing a propargylic alkoxy group has been observed to preferentially undergo [1,2]-acyl shift over [1,3]-shift. In addition, the complementary and contrasting reactivity of vinyl vs. alkynyl platinum carbenoids has been discovered. Vinyl platinum carbenoids are more prone to undergo [1,2]-H shift over addition to pi-bonds whereas alkynyl platinum carbenoids preferentially add to pi-bonds.

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页码：2719 / 2723

页数：5

相关论文

共 44 条

[1] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].

Buzas, A ;

Istrate, F ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (09) :1957-1959

[2] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615

[3] Reactivity and selectivity of 1,3-diyn-6-enes in electrophilic transition metal-catalyzed reactions [J].

Cho, Eun Jin ;

Kim, Mansuk ;

Lee, Daesung .

ORGANIC LETTERS, 2006, 8 (23) :5413-5416

[4] Metal-catalyzed bond reorganization of 1,3-diynes [J].

Cho, Eun Jin ;

Kim, Mansuk ;

Lee, Daesung .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) :3074-3078

[5] Golden carousel in catalysis: The cationic gold/propargylic ester cycle [J].

Correa, Andrea ;

Marion, Nicolas ;

Fensterbank, Louis ;

Malacria, Max ;

Nolan, Steven P. ;

Cavallo, Luigi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :718-721

[6] Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids [J].

Davies, HML ;

Nikolai, J .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) :4176-4187

[7]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[8] Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: Evidence for chirality transfer [J].

Fehr, Charles ;

Galindo, Jose .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2901-2904

[9] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[10] Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes [J].

Fürstner, A ;

Davies, PW ;

Gress, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8244-8245

← 1 2 3 4 5 →