Pd-Catalyzed Heck-Type Cascade Reactions with N-Tosyl Hydrazones: An Efficient Way to Alkenes via in Situ Generated Alkylpalladium

被引：95

作者：

Liu, Xianglei ^{[1
]}

Ma, Xinna ^{[1
]}

Huang, Yunze ^{[1
]}

Gu, Zhenhua ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 18期

关键词：

CROSS-COUPLING REACTIONS; CARBENE INSERTION; MIGRATORY INSERTION; TERMINAL ALKYNES; DIAZO-COMPOUNDS; BOND FORMATION; VINYL HALIDES; METAL CARBENE; TOSYLHYDRAZONES; ARYL;

D O I：

10.1021/ol402210a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed Heck-type cascade reaction of aryl halides and N-tosyl hydrazones is reported. The neopentylpalladium species;generated from an intramolecular Heck-type insertion reaction of aryl halides, could efficiently react with carbenes to form highly functionalized alkenes. The synthesis of spiro compounds was also explored via a multiple Heck-type insertion reaction with N-tosyl hydrazone.

引用

页码：4814 / 4817

页数：4

共 61 条

[1]

Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO

[2]

2-9

[3] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].

ANCIAUX, AJ ;

HUBERT, AJ ;

NOELS, AF ;

PETINIOT, N ;

TEYSSIE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :695-702

[4] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Moriel, Patricia ;

Amar, Fernando ;

Valdes, Carlos .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4792-4795

[5] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].

Barluenga, José ;

Moriel, Patricia ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590

[6] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[7] Synthesis of Polysubstituted Olefins by Pd-Catalyzed Cross-Coupling Reaction of Tosylhydrazones and Aryl Nonaflates [J].

Barluenga, Jose ;

Florentino, Lucia ;

Aznar, Fernando ;

Valdes, Carlos .

ORGANIC LETTERS, 2011, 13 (03) :510-513

[8] Synthesis of Dienes by Palladium-Catalyzed Couplings of Tosylhydrazones with Aryl and Alkenyl Halides [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Aznar, Fernando ;

Valdes, Carlos .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3235-3240

[9] Synthesis of 2-Arylacrylates from Pyruvate by Tosylhydrazide-Promoted Pd-Catalyzed Coupling with Aryl Halides [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Aznar, Fernando ;

Valdes, Carlos .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (43) :12801-12803

[10] Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides [J].

Barluenga, Jose ;

Escribano, Maria ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) :6856-6859

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