Hydroamination reactions catalyzed by [Au2(μ-Cl)(μ-bis(phosphino)ferrocene)][BArF24]

In this study, a series of [Au2Cl2(μ-PP)] (μ-PP = 1,1′-bis(diphenylphosphino)ferrocene (dppf), 1,1′-bis(diiso-propylphosphino)ferrocene (dippf), 1,1′-bis(dicyclohexylphosphino)ferrocene (dcpf), 1,1′- bis(ditert-butylphosphino)ferrocene (dtbpf), 1-diphenylphosphino-1′-ditert-butylphosphinoferrocene (dppdtbpf) or 1,1ʹ-bis(5-methyl-2-furanylphosphino)ferrocene (dfurpf)) compounds were examined as catalysts for the intramolecular ring-closing hydroamination of 3-(vinyloxy)propan-1-amine and the intermolecular hydroamination of phenylacetylene with a variety of phenylamine reagents. The catalytic activity of the corresponding [Au2(μ-Cl)(μ-PP)][BArF24] compounds that were generated in situ was also explored. Two new [Au2Cl2(μ-PP)] compounds with chiral bis(phosphino)ferrocene ligands (PP = 1,1′-bis(2R,5R-dimethylphospholanyl)ferrocene (R-dMeplf) or 1,1′-bis(2S,5S-dimethylphospholanyl)ferrocene (S-dMeplf)) were prepared, characterized spectroscopically and electrochemically, and evaluated as catalysts in the ring-closing hydroamination reaction. In addition, the X-ray structures of [Au2Cl2(μ-PP)] (PP = dppdtbpf, R-dMeplf and S-dMeplf) were determined.Graphical abstract

Source: Journal of Organometallic Chemistry - November 28, 2019 Category: Chemistry Source Type: research