Synthesis and Characterization of Chiral Gold (I) Phosphine Complexes with New Dithiophosphorus Ligands

Abstract

The novel chiral-centered amidodithiophosphonates [Fe(η⁵-C₅H₅)(η⁵-C₅H₄P(= S)(SH)(NHR))] were synthesized by the reaction of [FcP(= S)(μ-S)]₂ and chiral amines such as (R)-(+)-1-phenylethyl-amine, (S)-(−)-1-phenylethyl-amine, (R)-(+)-1-phenylpropyl-amine, (S)-(+)-3-methyl-2-butyl-amine, (S)-(+)-1-aminoindane, (-)-cis-myrtanylamine, and (1S,2S)-(+)-2-benzyloxycyclohexyl-amine in toluene. The reaction of chiral-centered amidoferrocenyldithiophosphonates and [(PPh₃)AuCl] gave rise to gold (I) complexes in CHCl₃ or the CHCl₃-toluene mixtures. The ligands 1–7 and the complexes 1a, 3a, and 4a were characterized by elemental analyses, infrared (IR), nuclear magnetic resonance (NMR; ¹H‒, ³¹P‒, ¹³C‒) spectroscopy, as well as mass spectrometry (MS) measurements. Although amidodithiophosphonates are potential tridentate ligands, they are coordinated to gold only by one sulfur atom. The investigated chiral gold (I) complexes including two different phosphorus ligands are air stable.

GRAPHICAL ABSTRACT

Keywords:

• Amidodithiophosphonate
• chiral compounds
• ferrocenyldithiophosphonate
• gold (I) complexes
• triphenylphosphine

Acknowledgments

This study was supported by Turkish Council of Research and Technology, TUBITAK (Grant no. 107T817).