Synthesis of Ar-SF4Cl and Ar-SF5 Compounds from Arylphosphorothiolates

Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF4Cl and Ar-SF5 Synthesis: L. Wang, S. Ni, J. Cornella
Synthesis 2021, 53, DOI: 10.1055/s-0040-1706039
The pentafluorosulfanyl group (SF5) has been only marginally studied over the last century, but there is now growing interest in SF5 compounds, especially in areas such as agrochemistry, drug discovery and materials science. Recently, the group of Dr. Josep Cornella from the Max-Planck-Institut für Kohlenforschung (Mülheim an der Ruhr, Germany), reported a novel approach to aryl-SF5 and related aryl-SF4Cl derivatives.

Dr. Cornella said: “The introduction of SF5 groups into aryl molecules is an area of high interest for the medicinal and agrochemical community, as it represents a highly hydrophobic and fluorinated functional group with interesting properties. Yet, its widespread presence in compounds is somewhat limited, mainly due to the limited and scattered approaches known for its synthesis. Herein, we provide a unified approach where arylphosphorothiolates are oxidized to the corresponding Ar-SF4Cl, precursors of the coveted Ar-SF5. The phosphorothiolate moiety represents an attractive unifying functional group as it can be easily accessed from cheap and readily available material such as aryl boronic acids, aryl halides or even aromatic C–H bonds. Although still far from ideal, this approach provides a convergent platform to the synthesis of such challenging compounds.”

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