A general and practical Ni-catalyzed C-H perfluoroalkylation of (hetero)arenes

被引:25
作者
Zhang, Shaoke [1 ]
Rotta-Loria, Nicolas [2 ]
Weniger, Florian [1 ]
Rabeah, Jabor [1 ]
Neumann, Helfried [1 ]
Taeschler, Christoph [3 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock eV, Leibniz Inst Katalyse, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] Dalhousie Univ Halifax, Dept Chem, Halifax, NS B3H 4R2, Canada
[3] Lonza Ltd, Rottenstr 6, CH-3930 Visp, Switzerland
关键词
HETEROAROMATIC-COMPOUNDS; AROMATIC-COMPOUNDS; OXIDATIVE TRIFLUOROMETHYLATION; FLUORINE; FLUOROALKYLATION; ARENES; CHLORIDES; PRECATALYST; CHEMISTRY; INSIGHTS;
D O I
10.1039/c9cc01971e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A direct perfluoroalkylation of (hetero) arenes using the air- and moisture-stable complex (dppf)Ni(o-tol)Cl was developed (23 examples). The novel procedure allows for the synthesis of various fluorinated products and tolerates sensitive functional groups including aldehydes, free amino groups and several heterocycles.
引用
收藏
页码:6723 / 6726
页数:4
相关论文
共 63 条
[1]   Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides [J].
Aikawa, Kohsuke ;
Nakamura, Yuzo ;
Yokota, Yuki ;
Toya, Wataru ;
Mikami, Koichi .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (01) :96-100
[2]   Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents [J].
Bao, Xifei ;
Liu, Lihua ;
Li, Junlan ;
Fan, Shilu .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :463-468
[3]   Radical Fluoroalkylation Reactions [J].
Barata-Vallejo, Sebastian ;
Victoria Cooke, Maria ;
Postigo, Al .
ACS CATALYSIS, 2018, 8 (08) :7287-7307
[4]   Perfluoroalkylation reactions of (hetero)arenes [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
RSC ADVANCES, 2015, 5 (77) :62498-62518
[5]   A room temperature cyanation of (hetero) aromatic chlorides by an air stable nickel(II) XantPhos precatalyst and Zn(CN)2 [J].
Beattie, D. Dawson ;
Schareina, Thomas ;
Beller, Matthias .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) :4291-4294
[6]   Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale [J].
Beatty, Joel W. ;
Douglas, James J. ;
Miller, Richard ;
McAtee, Rory C. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
CHEM, 2016, 1 (03) :456-472
[7]  
Biza T., 2008, J FLUORINE CHEM, V129, P235
[8]   Fluorinated sulfoximines: syntheses, properties and applications [J].
Bizet, Vincent ;
Kowalczyk, Rafal ;
Bolm, Carsten .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2426-2438
[9]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[10]   Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304