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
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
收藏
页码:13291 / 13294
页数:4
相关论文
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