Elucidation of the reaction mechanism for the palladium-catalyzed synthesis of vinyl acetate

被引:61
作者
Stacchiola, D
Calaza, F
Burkholder, L
Schwabacher, AW
Neurock, M
Tysoe, WT [1 ]
机构
[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53211 USA
[2] Univ Wisconsin, Surface Studies Lab, Milwaukee, WI 53211 USA
[3] Univ Virginia, Dept Chem Engn, Charlottesville, VA 22904 USA
关键词
IR spectroscopy; isotopes; palladium; reaction mechanisms; surface chemistry;
D O I
10.1002/anie.200500782
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Finding the right pathway: Reaction of isotopomers of ethylene with acetate species (see scheme) adsorbed on a Pd(111) surface in ultrahigh vacuum has shown that vinyl acetate is produced by insertion of ethylene into the acetate species to form an acetoxyethyl intermediate, which decomposes by β-hydride elimination to yield vinyl acetate. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4572 / 4574
页数:3
相关论文
共 50 条
[41]   Selective Palladium-Catalyzed α,β-Homodiarylation of Vinyl Esters in Aqueous Medium [J].
Trzepizur, Damian ;
Brodzka, Anna ;
Koszelewski, Dominik ;
Wilk, Monika ;
Ostaszewski, Ryszard .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) :6028-6036
[42]   Synthesis of ferrocene amides and α-ketoamides via palladium-catalyzed homogeneous carbonylation reaction [J].
Szarka, Z ;
Skoda-Földes, R ;
Kuik, A ;
Berente, Z ;
Kollár, L .
SYNTHESIS-STUTTGART, 2003, (04) :545-550
[43]   Synergistic Steric Effects in the Development of a Palladium-Catalyzed Alkyne Carbohalogenation: Stereodivergent Synthesis of Vinyl Halides [J].
Le, Christine M. ;
Menzies, Perry J. C. ;
Petrone, David A. ;
Lautens, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) :254-257
[44]   A Combined Experimental/Computational Study of the Mechanism of a Palladium-Catalyzed Bora-Negishi Reaction [J].
Campos, Jesus ;
Nova, Ainara ;
Kolychev, Eugene L. ;
Aldridge, Simon .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (51) :12655-12667
[45]   Direct synthesis of protected arylacetaldehydes by tetrakis(phosphane)palladium-catalyzed arylation of ethyleneglycol vinyl ether [J].
Kondolff, I ;
Doucet, H ;
Santelli, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (03) :765-774
[46]   Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction [J].
McAtee, Jesse R. ;
Martin, Sara E. S. ;
Ahneman, Derek T. ;
Johnson, Keywan A. ;
Watson, Donald A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) :3663-3667
[47]   Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate [J].
Lindh, Jonas ;
Savmarker, Jonas ;
Nilsson, Peter ;
Sjoberg, Per J. R. ;
Larhed, Mats .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (18) :4630-4636
[48]   Palladium-catalyzed synthesis of substituted hydantoins - A new carbonylation reaction for the synthesis of amino acid derivatives [J].
Beller, M ;
Eckert, M ;
Moradi, WA ;
Neumann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (10) :1454-1457
[49]   Palladium-Catalyzed Carbonylative Synthesis of Functionalized Benzimidazopyrimidinones [J].
Mancuso, Raffaella ;
Veltri, Lucia ;
Russo, Patrizio ;
Grasso, Giuseppe ;
Cuocci, Corrado ;
Romeo, Roberto ;
Gabriele, Bartolo .
SYNTHESIS-STUTTGART, 2018, 50 (02) :267-277
[50]   Palladium-Catalyzed Dual Catalytic Synthesis of Heterocycles [J].
Ballav, Tamal ;
Chakrabortty, Rajesh ;
Das, Aniruddha ;
Ghosh, Suman ;
Ganesh, Venkataraman .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (30)