A Selective Palladium-Catalyzed Carbonylative Arylation of Aryl Ketones to Give Vinylbenzoate Compounds

被引:34
作者
Schranck, Johannes [1 ]
Tlili, Anis [1 ]
Neumann, Helfried [1 ]
Alsabeh, Pamela G. [2 ]
Stradiotto, Mark [2 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[2] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4R2, Canada
关键词
carbonylation; enols; homogeneous catalysis; palladium; vinyl esters; ALPHA-ARYLATION; CARBOXYLIC-ACIDS; ENOL ESTERS; STEREOSELECTIVE-SYNTHESIS; HETEROARYL BROMIDES; TERMINAL ALKYNES; RHODIUM(I) COMPLEXES; COUPLING REACTIONS; GENERAL-SYNTHESIS; HECK REACTION;
D O I
10.1002/chem.201202895
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Preparation of enols: When treated with [{Pd(cinnamyl)Cl} 2]/cataCXium A (nBuPAd2, Ad=adamantyl) under an atmosphere of CO, aryl ketones react with aryl halides in a carbonylative C-O coupling reaction to form (Z)-vinyl benzoates (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:15592 / 15597
页数:6
相关论文
共 50 条
[11]   Palladium-Catalyzed Carbonylative α-Arylation of 2-Oxindoles with (Hetero) aryl Bromides: Efficient and Complementary Approach to 3-Acyl-2-oxindoles [J].
Lian, Zhong ;
Friis, Stig D. ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9582-9586
[12]   Selective Palladium-Catalyzed Aminocarbonylation of Aryl Halides with CO and Ammonia [J].
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9750-9753
[13]   Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones [J].
Peng, Jin-Bao ;
Chen, Bo ;
Qi, Xinxin ;
Ying, Jun ;
Wu, Xiao-Feng .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) :4153-4160
[14]   Progress in the palladium-catalyzed α-arylation of ketones with chloroarenes [J].
Ehrentraut, A ;
Zapf, A ;
Beller, M .
ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (02) :209-217
[15]   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
[16]   Palladium-Catalyzed Carbonylative Transformations of Bromhexine into Bioactive Compounds as Glucocerebrosidase Inhibitors [J].
Sharif, Muhammad ;
Pews-Davtyan, Anahit ;
Lukas, Jan ;
Schranck, Johannes ;
Langer, Peter ;
Rolfs, Arndt ;
Beller, Matthias .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (01) :222-230
[17]   Palladium-Catalyzed Carbonylative Sonogashira Transformations: Advancements and Insights [J].
Vishnu, Prasanth ;
Saranya, Padinjare Veetil ;
Anilkumar, Gopinathan .
CHEMICAL RECORD, 2025, 25 (05)
[18]   Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones [J].
Donohoe, Timothy J. ;
Pilgrim, Ben S. ;
Jones, Geraint R. ;
Bassuto, Jose A. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (29) :11605-11608
[19]   Supported Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Aryl Bromides and Arylboronic Acids [J].
Xu, Tiefeng ;
Wang, Qi ;
Yang, Zeyi ;
Yi, Lili ;
Wang, Jian-Shu ;
Lu, Wangyang ;
Ying, Jun ;
Wu, Xiao-Feng .
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (15) :2027-2030
[20]   Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: a straightforward procedure for the synthesis of aryl trifluoromethyl ketones [J].
Zhu, Fengxiang ;
Yang, Guangfu ;
Zhou, Shaolin ;
Wu, Xiao-Feng .
RSC ADVANCES, 2016, 6 (62) :S7070-S7074