Fe(III)-Catalyzed Synthesis of 1-Chalcogenylated Naphthalene Derivatives

Chalcogenylation of Naphthalene Derivatives Catalyzed by Iron(III) Chloride and Potassium Iodide: D. Seckler, E. Q. da Luz, G. L. Silvério, G. Badshah, D. B. Lima, E. A. Abreu, B. Albach, R. R. Ribeiro, D. S. Rampon
Synlett 2021, 31, DOI: 10.1055/s-0040-1706748
Naphthalene derivatives carrying a sulfur or selenium atom are valuable compounds in a number of areas, such as materials science, drug discovery and agrochemistry. Chemoselective incorporation of sulfenylated or selenylated functions is onto the naphthalene scaffold is particularly valuable as these versatile compounds could then be readily oxidized and synthetically manipulated to access a range of additional compounds, such as the corresponding sulfoxides, sulfones and selenoxides. Recently, the group of Professor Daniel da Silveira Rampon from the Federal University of Paraná (Curitiba, Brazil) reported an effective strategy for preparing the title compounds.

Professor Rampon said: “We have been pleased to find that cheap and safe reagents, such as FeCl3 and KI, were able to catalyze the selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se). We hope that findings from this research can further help accessing other new organochalcogen compounds.”

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