Gold-Catalyzed Suzuki Coupling of ortho-Substituted Hindered Aryl Substrates

被引:27
作者
Dwadnia, Nejib [1 ]
Roger, Julien [1 ]
Pirio, Nadine [1 ]
Cattey, Helene [1 ]
Ben Salem, Ridha [2 ]
Hierso, Jean-Cyrille [1 ,3 ]
机构
[1] Univ Bourgogne, UBFC, CNRS, Inst Chim Mol,UMR 6302, 9 Ave Alain Savary, F-21078 Dijon, France
[2] Univ Sfax, Fac Sci, Lab Chim Organ Phys UR11ES74, Sfax 3038, Tunisia
[3] IUF, 103 Blvd St Michel, F-75005 Paris, France
关键词
COMPLEXES; GOLD(III); NANOPARTICLES; REACTIVITY; BROMIDES; HALIDES; ACIDS;
D O I
10.1002/asia.201601583
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method that allows hindered ortho-substituted aryl iodides to be efficiently coupled to phenylboronic acid using a gold-catalyzed C-C bond formation is presented. The use of a molecularly-defined dinuclear gold chloride catalytic precursor that is stabilized by a new tetradentate (N,N')-diamino-(P,P')-diphosphino ferrocene hybrid ligand in a Suzuki-type reaction is described for the first time. Electron-rich isopropyl groups on phosphorus were found essen-tial for a superior activity, while the performances of a set of analogous gold dinuclear complexes that were fully characterized by multinuclear NMR spectroscopy and XRD analysis, were investigated. Therefore, arylation of para and orthosubstituted iodoarenes bearing electron-rich, electron-poor functional groups, and even hindered polycyclic aromatic compounds is described.
引用
收藏
页码:459 / 464
页数:6
相关论文
共 27 条
[1]   Converging and Diverging Synthetic Strategies to Tetradentate (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation [J].
Allouch, Fatima ;
Dwadnia, Nejib ;
Vologdin, Nikolay V. ;
Svyaschenko, Yurii V. ;
Cattey, Helene ;
Penouilh, Marie-Jose ;
Roger, Julien ;
Naoufal, Daoud ;
Ben Salem, Ridha ;
Pirio, Nadine ;
Hierso, Jean-Cyrille .
ORGANOMETALLICS, 2015, 34 (20) :5015-5028
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]  
[Anonymous], 2007, ANGEW CHEM-GER EDIT
[4]   A reassessment of the transition-metal free Suzuki-type coupling methodology [J].
Arvela, RK ;
Leadbeater, NE ;
Sangi, MS ;
Williams, VA ;
Granados, P ;
Singer, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168
[5]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[6]   New heterogenized gold(I)-heterocyclic carbene complexes as reusable catalysts in hydrogenation and cross-coupling reactions [J].
Corma, A. ;
Gutierrez-Puebla, E. ;
Iglesias, M. ;
Monge, A. ;
Perez-Ferreras, S. ;
Sanchez, F. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1899-1907
[7]   Heterogenized gold(I), gold(III), and Palladium(II) complexes for C-C bond reactions [J].
Corma, Avelino ;
Gonzalez-Arellano, Camino ;
Iglesias, Marta ;
Perez-Ferreras, Susana ;
Sanchez, Felix .
SYNLETT, 2007, (11) :1771-1774
[8]   Suzuki-Miyaura cross-coupling reaction between aryl halides and phenylboronic acids over gold nano-particles supported on MgO (or CaO) and other metal oxides [J].
Dumbre, D. K. ;
Yadav, P. N. ;
Bhargava, S. K. ;
Choudhary, V. R. .
JOURNAL OF CATALYSIS, 2013, 301 :134-140
[9]   Aminomethyl-Substituted Ferrocenes and Derivatives: Straightforward Synthetic Routes, Structural Characterization, and Electrochemical Analysis [J].
Dwadnia, Nejib ;
Allouch, Fatima ;
Pirio, Nadine ;
Roger, Julien ;
Cattey, Helene ;
Fournier, Sophie ;
Penouilh, Marie-Josee ;
Devillers, Charles H. ;
Lucas, Dominique ;
Naoufal, Daoud ;
Ben Salem, Ridha ;
Hierso, Jean-Cyrille .
ORGANOMETALLICS, 2013, 32 (20) :5784-5797
[10]   Gold-Catalyzed Cross-Couplings: New Opportunities for C-C Bond Formation [J].
Garcia, Pierre ;
Malacria, Max ;
Aubert, Corinne ;
Gandon, Vincent ;
Fensterbank, Louis .
CHEMCATCHEM, 2010, 2 (05) :493-497