RESUMEN
Two new NHC adducts of cyclopalladated ferrocenylpyrazine complexes 1-2 have been prepared and characterized. An efficient NHC-modulated Pd/Cu cocatalyzed three-component coupling reaction for the synthesis of 2,6-diarylquinolines from aminobenzyl alcohols, aryl ketones, and arylboronic acids in air is described. The reaction involves oxidation, cyclization and Suzuki reactions. The luminescence of the resulting arylquinolines 3-30 was also investigated.
Asunto(s)
Cobre/química , Diarilquinolinas/síntesis química , Compuestos Heterocíclicos/química , Metano/análogos & derivados , Paladio/química , Catálisis , Diarilquinolinas/química , Metano/química , Conformación Molecular , Espectrometría de FluorescenciaRESUMEN
In the title compound, [Fe(C5H5)(C20H13N2O2)], the substituted cyclo-penta-dienyl ring and quinoline system are approximately coplanar, making a dihedral angle of 5.18â (6)°, while the dihedral angle between the quinoline system and the benzene ring is 28.45â (8)°. There is high thermal motion in the free cyclo-penta-dienyl ring compared with the substituted cyclo-penta-dienyl ring. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.
RESUMEN
An efficient PPh3-cyclometalated iridium(III) benzo[h]quinoline hydride 1/Pd(OAc)2-cocatalyzed three-component α-alkylation/Suzuki reaction has been developed. The three-component reaction of 4-bromobenzyl alcohol, acetylferrocene, and arylboronic acids gives ferrocenyl ketones containing biaryls in moderate to good yields. This method was successfully applied to a one-pot synthesis of 6-aryl-2-ferrocenyl quinolines, using (2-amino-5-bromophenyl)methanol instead of 4-bromobenzyl alcohol.