Gold-Catalyzed Suzuki Coupling of ortho-Substituted Hindered Aryl Substrates
Nejib Dwadnia1, Julien Roger1, Nadine Pirio1
1Université de Bourgogne, Institut de Chimie Moléculaire de l'Université de Bourgogne, UMR-CNRS 6302-Université de Bourgogne Franche-Comté (UBFC), 9, avenue Alain Savary, 21078, Dijon, France.
Abstract:
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 essential 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 ortho-substituted iodoarenes bearing electron-rich, electron-poor functional groups, and even hindered polycyclic aromatic compounds is described.
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