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
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 49期
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
[31]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[32]   Palladium-Catalyzed Direct Arylation of Heteroarenes with Aryl Mesylates [J].
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) :761-765
[33]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[34]   Palladium-Catalyzed Carbonylative Cyclization of Azoarenes [J].
Wang, Zechao ;
Yin, Zhiping ;
Zhu, Fengxiang ;
Li, Yahui ;
Wu, Xiao-Feng .
CHEMCATCHEM, 2017, 9 (19) :3637-3640
[35]   Palladium-catalyzed benzylic C(sp3)-H carbonylative arylation of azaarylmethyl amines with aryl bromides [J].
Zhao, Haoqiang ;
Hu, Bowen ;
Xu, Lijin ;
Walsh, Patrick J. .
CHEMICAL SCIENCE, 2021, 12 (32) :10862-10870
[36]   Access to β-Keto Esters by Palladium-Catalyzed Carbonylative Coupling of Aryl Halides with Monoester Potassium Malonates [J].
Korsager, Signe ;
Nielsen, Dennis U. ;
Taaning, Rolf H. ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9763-9766
[37]   Palladium-catalyzed direct arylation of (hetero)arenes with aryl boronic acids [J].
Yang, Shang-Dong ;
Sun, Chang-Liang ;
Fang, Zhao ;
Li, Bi-He ;
Li, Yi-Zhou ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1473-1476
[38]   Palladium-Catalyzed Dehydrogenative β-Arylation of Simple Saturated Carbonyls by Aryl Halides [J].
Gandeepan, Parthasarathy ;
Rajamalli, P. ;
Cheng, Chien-Hong .
ACS CATALYSIS, 2014, 4 (12) :4485-4489
[39]   Palladium-catalyzed carbonylative cross-coupling reactions of pyridine halides and aryl boronic acids:: a convenient access to α-pyridyl ketones [J].
Couve-Bonnaire, S ;
Carpentier, JF ;
Mortreux, A ;
Castanet, Y .
TETRAHEDRON LETTERS, 2001, 42 (22) :3689-3691
[40]   Palladium-catalyzed carbonylative synthesis of alkynones from aryl iodides and phenylpropiolic acid employing formic acid as the CO source [J].
Li, Chong-Liang ;
Zhang, Wan-Quan ;
Qi, Xinxin ;
Peng, Jin-Bao ;
Wu, Xiao-Feng .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 838 :9-11
12345