1,1'-bis(phosphino)ferrocene ligands are of interest in catalytic studies as the properties of the phosphorus donor atoms can be altered by changing the phosphine substituents. Additionally, the ferrocene backbone provides unique electronic and conformational flexibility to these ligands. Previous investigations in our lab found that gold compounds with bis(phosphino)ferrocene ligands, [Au2Cl2(μ-PP)], react with sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, Na[BArF24], to generate cationic species with the general formula [Au2(μ-Cl)(μ-PP)][BArF24]. The [Au2(μ-Cl)(μ-PP)]+ compounds were found to give significantly improved catalytic efficiency in a series of ring-closing reactions as compared to the [Au2Cl2(μ-PP)] compounds. Herein we report the intramolecular ring-closing hydroamination of 3-(vinyloxy)propan-1-amine and the intermolecular hydroamination of phenylacetylene with a variety of phenylamine reagents, using a series of [Au2Cl2(μ-PP)] (μ-PP = 1,1'-bis(diphenylphosphino)ferrocene (dppf), 1,1'-bis(diiso-propylphosphino)ferrocene (dippf), 1,1'-bis(dicylohexylphosphino)ferrocene (dcpf), 1,1'- bis(ditert-butylphosphino)ferrocene (dtbpf), 1-diphenylphosphino-1'-ditert- butylphosphinoferrocene (dppdtbpf) or 1,1’-bis(5-methyl-2-furanylphosphino)ferrocene (dfurpf)) compounds as catalysts. The catalytic activity corresponding [Au2(μ-Cl)(μ-PP)][BArF24] compounds was also examined.

Hydroamination reactions catalyzed by gold compounds with bis(phosphino)ferrocene ligands

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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