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The synthesis of new 4-(diphenylphosphino)-phenothiazine derivatives was achieved by a regioselective lithiation of the thio-aryl structural unit of the phenothiazine precursor, followed by in situ reaction of the intermediate with chloro-diphenylphosphine. Symmetrical 4,6-bis(diphenylphosphino)-phenothiazine was obtained by similar functionalization of the isolated 4-(diphenylphosphino)-phenothiazine. These air stable aryl-phosphines were purified by column chromatography and characterized by MS, FT-IR, ¹H-, ¹³C- and ³¹P-NMR spectroscopy. Coordination of 10-alkyl-4-(diphenyl-phosphino)-phenothiazines to Pd(II) was confirmed by means of ³¹P-NMR spectroscopy which indicated a strong deshielding effect upon P atoms.

Keywords: Phenothiazine, Heteroaryl-diphenylphosphine, Pd(II) complex, ³¹P-NMR