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
[21]   Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids [J].
Couve-Bonnaire, S ;
Carpentier, JF ;
Mortreux, A ;
Castanet, Y .
TETRAHEDRON, 2003, 59 (16) :2793-2799
[22]   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
[23]   Palladium-Catalyzed Direct α-Arylation of Methane Sulfonamides with Aryl Bromides [J].
Gao, Gui ;
Chen, Xiang-Zhu ;
Wang, Zhong-Yu ;
Zhang, Yuan-Yuan ;
Liu, Jing-Jing ;
Hou, Shi-Cong .
CHEMISTRYSELECT, 2018, 3 (07) :2152-2156
[24]   Palladium-catalyzed carbonylative coupling of benzyl chlorides with aryl boronic acids in aqueous media [J].
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
TETRAHEDRON LETTERS, 2010, 51 (47) :6146-6149
[25]   Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates [J].
Yuen, On Ying ;
Chen, Xiangmeng ;
Wu, Junyu ;
So, Chau Ming .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (12) :1912-1916
[26]   PALLADIUM-CATALYZED SELECTIVE α-ARYLATION OF ORTHO-BROMOACETOPHENONES [J].
Krishna, Jonnada ;
Reddy, Alavala Gopi Krishna ;
Satyanarayana, Gedu .
SYNTHETIC COMMUNICATIONS, 2014, 44 (14) :2103-2111
[27]   Palladium-Catalyzed Carbonylative Heck Reaction of Aryl Bromides with Vinyl Ethers to 3-Alkoxy Alkenones and Pyrazoles [J].
Schranck, Johannes ;
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) :4827-4831
[28]   Palladium-Catalyzed Carbonylative Synthesis of Heterocycles [J].
Feng, Jian-Bo ;
Wu, Xiao-Feng .
HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2017, 121 :207-246
[29]   Palladium-Catalyzed β-Selective Direct Arylation of Porphyrins [J].
Kawamata, Yu ;
Tokuji, Sumito ;
Yorimitsu, Hideki ;
Osuka, Atsuhiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8867-8870
[30]   Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides [J].
Zheng, Bing ;
Li, Minyan ;
Gao, Gui ;
He, Yuying ;
Walsh, Patrick J. .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) :2156-2162