ABSTRACT
We describe the oxygenation of tertiary arylamines, and the amination of tertiary arylamines and phenols. The key step of these coupling reactions is an iron-catalyzed oxidative C-O or C-N bond formation which generally provides the corresponding products in high yields and with excellent regioselectivity. The transformations are accomplished using hexadecafluorophthalocyanine-iron(II) (FePcF16 ) as catalyst in the presence of an acid or a base additive and require only ambient air as sole oxidant.
ABSTRACT
We describe the synthesis and photophysical properties of tetraarylnaphthidines. Our synthetic approach is based on an iron-catalyzed oxidative C-C coupling reaction as the key step using a hexadecafluorinated iron-phthalocyanine complex as a catalyst and air as the sole oxidant. The N,N,N',N'-tetraarylnaphthidines proved to be highly fluorescent with quantum yields of up to 68%.
Subject(s)
Chemistry Techniques, Synthetic , Ferrous Compounds/chemistry , Iron/chemistry , Photochemical Processes , Catalysis , Ferrous Compounds/chemical synthesis , Fluorescence , Molecular Conformation , Molecular Structure , Oxidative Coupling , Spectrum AnalysisABSTRACT
A mild procedure for the oxidative C-C cross-coupling of tertiary anilines with phenols is described which provides the products generally in high yields and with excellent selectivity. The reaction is catalyzed by the hexadecafluorinated iron-phthalocyanine complex FePcF16 in the presence of substoichiometric amounts of methanesulfonic acid and ambient air as sole oxidant.
