Pd-Catalyzed C=C Double-Bond Formation by Coupling of N-Tosylhydrazones with Benzyl Halides

被引：161

作者：

Xiao, Qing

Ma, Jian

Yang, Yang

Zhang, Yan

Wang, Jianbo ^{[1
]}

机构：

[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

关键词：

ALPHA-DIAZOCARBONYL COMPOUNDS; CARBENE INSERTION; STEREOSELECTIVE-SYNTHESIS; ORGANIC-SYNTHESIS; VINYL HALIDES; PALLADIUM; ARYLATION; WITTIG; ARYL; DIAZOESTERS;

D O I：

10.1021/ol901876w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed reaction of N-tosylhydrazones with benzyl halides affords di- and trisubstituted olefins in high yields with excellent stereoselectivity. This coupling reaction is supposed to proceed through a migratory insertion of Pd carbene species.

引用

收藏

页码：4732 / 4735

页数：4

相关论文

共 46 条

[1] RECENT APPLICATIONS OF THE SHAPIRO REACTION [J].

ADLINGTON, RM ;

BARRETT, AGM .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) :55-59

[2] Aryl palladium carbene complexes and carbene-aryl coupling reactions [J].

Albéniz, AC ;

Espinet, P ;

Manrique, R ;

Pérez-Mateo, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (05) :1565-1573

[3] THE DECOMPOSITION OF TOLUENE-PARA-SULPHONYLHYDRAZONES BY ALKALI [J].

BAMFORD, WR ;

STEVENS, TS .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC) :4735-4740

[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] OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS [J].

BOUTAGY, J ;

THOMAS, R .

CHEMICAL REVIEWS, 1974, 74 (01) :87-99

[7] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2007, 9 (26) :5397-5400

[8] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[9] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[10] Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds [J].

Chen, Shufeng ;

Wang, Jianbo .

CHEMICAL COMMUNICATIONS, 2008, (35) :4198-4200

← 1 2 3 4 5 →