Exploiting the Reactivity of Fluorinated 2-Arylpyridines in Pd-Catalyzed C-H Bond Arylation for the Preparation of Bright Emitting Iridium(III) Complexes.

Pd-catalyzed C-H bond arylation applied to 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine () and 2-(3,5-difluorophenyl)-5-(trifluoromethyl)pyridine () allows the access to two families of Ir(III) complexes, charge-neutral and cationic species. The reaction is regioselective since only the C3- or C4-position of the fluorinated phenyl ring of or is readily functionalized - namely the C-H bond flanked by the two fluorine atoms which is the most acidic - which allows the electronic control of the reactive site. A range of electron-withdrawing (CN, COEt, C(O)Me) substituents on the aryl group has been incorporated leading to the pro-ligands (, Ar-2,4-dFppy; , Ar = -CH-CN; , Ar = -CH-COEt; , Ar = -CH-C(O)Me; , and Ar-3,5-dFppy; , Ar = -CH-COEt).

Crystal structure and Hirshfeld surface analysis of tris-(2,2'-bi-pyridine)-nickel(II) bis-(1,1,3,3-tetra-cyano-2-eth-oxy-propenide) dihydrate.

The title compound, [Ni(CHN)](CHNO)·2HO, crystallizes as a racemic mixture in the monoclinic space group 2/. In the crystal, the 1,1,3,3-tetracyano-2-ethoxypropenide anions and the water molecules are linked by O-H⋯N hydrogen bonds, forming chains running along the [010] direction. The bpy ligands of the cation are linked to the chain C-H⋯π(cation) inter-actions involving the CH group.