Platinum(II)-Catalyzed Cross-Coupling of Polyfluoroaryl Imines

Abstract

The introduction of fluorine into an organic molecule imparts unique physicochemical properties. Not surprisingly, fluorine is increasingly incorporated into new drugs and agrochemicals. However, aryl fluoride building blocks are only available through synthesis. The ability to cross-couple polyfluoroaromatics selectively could provide a convenient route to functionalized fluoroaromatics. We report herein the first examples of Pt-catalyzed cross-coupling of aryl fluorides. The methylated products can potentially serve as precursors to a wide range of functionalized fluorinated small molecules.

Fluorine as a ligand substituent in organometallic chemistry: A second chance and a second research career

“…Much of this recent activity is driven by the need for synthetic procedures to incorporate fluorine or a CF 3 group strategically in the synthesis of pharmaceuticals or PET reagents, leading to the development of new methodology for formation of C-F and C-CF 3 bonds [110][111][112][113][114][115][116][117][118][119][120][121][122]. Organometallic chemistry involving the chemical functionalization of C-F bonds also continues to be an active field [123][124][125][126][127][128][129][130][131][132][133][134][135][136].…”

Pt(II)Cl2(DMSO)2-catalyzed cross-coupling of polyfluoroaryl imines

“…Such strategies have potential for use in fluorocarbon remediation. Over the last decade, considerable attention has been devoted to the selective activation and cross-coupling of polyfluorinated compounds [3][4][5]. Given the emergence of fluorine in bioactive molecules [6], such strategies have the potential for generating fluoroaromatic building blocks for use in pharmaceutical and industrial applications.…”

Activation and Formation of Aromatic C–F Bonds

“…82 and 83) [142,143]. Having Crespo and Martinez's stoichiometric Pt C-F activation studies [137] for inspiration, the Love group determined the Pt(II) dimer [(CH 3 ) 2 Pt (μ-SMe 2 )] 2 was an effective catalytic precursor for the cross-coupling reaction of polyfluorinated aryl imines and dialkyl zinc reagents.…”