Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions

被引：91

作者：

Barluenga, Jose ^{[1
]}

Escribano, Maria ^{[1
]}

Moriel, Patricia ^{[1
]}

Aznar, Fernando ^{[1
]}

Valdes, Carlos ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 48期

关键词：

cross-coupling; enamines; enol ethers; hydrazones; palladium; CARBENE INSERTION; ALPHA-ARYLATION; BOND FORMATION; ARYL BROMIDES; VINYL HALIDES; PALLADIUM; ALDEHYDES; CLEAVAGE;

D O I：

10.1002/chem.200902718

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

"Chemical Equation Presented" α-Substitution is fine: α-Alkoxycarbonyl and α-aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide-promoted Pd-catalyzed cross-coupling of carbonyls with aryl halides. The reac-tion gives rise to enol ethers and enamines, respectively, which are useful synthetic intermediates in heterocyclic synthesis. Otherwise, they can be hydrolyzed to give α,α- disubstituted aldehydes. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：13291 / 13294

页数：4

共 31 条

[21] Syntheses of fused heterocyclic compounds and their inhibitory activities for squalene synthase
Miki, T
Kori, M
Fujishima, A
Mabuchi, H
Tozawa, R
Nakmura, M
Sugiyama, Y
Yukimasa, H
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (02) : 385 - 400
[22] Negishi E., 2002, Handbook of Organopalladium Chemitry for Organic Synthesis
[23] Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a Heck triarylation process
Nilsson, P
Larhed, M
Hallberg, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) : 8217 - 8225
[24] Palladium-catalyzed cross-coupling of α-diazocarbonyl compounds with arylboronic acids
Peng, Cheng
Wang, Yan
Wang, Jianbo
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) : 1566 - +
[25] Direct acylation of aryl bromides with aldehydes by palladium catalysis
Ruan, Jiwu
Saidi, Ourida
Iggo, Jonathan A.
Xiao, Jianliang
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) : 10510 - +
[26] Direct transition metal-catalyzed functionalization of heteroaromatic compounds
Seregin, Ilya V.
Gevorgyan, Vladimir
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1173 - 1193
[27] Copper-catalyzed oxidative cleavage of carbon-carbon double bond of enol ethers with molecular oxygen
Tokunaga, M
Shirogane, Y
Aoyama, H
Obora, Y
Tsuji, Y
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (23) : 5378 - 5382
[28] Tsuji J., 2004, PALLADIUM REAGENTS C, DOI DOI 10.1002/0470021209.CH1
[29] Vo G. D., 2008, ANGEW CHEM, V120, P2157
[30] Palladium-catalyzed α-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos
Vo, Giang D.
Hartwig, John E.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) : 2127 - 2130

← 1 2 3 4 →