Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF4Cl and Ar-SF5 Synthesis

Lin Wang; Shengyang Ni; Josep Cornella

doi:10.1055/s-0040-1706039

Synthesis, Table of Contents

Synthesis 2021; 53(22): 4308-4312
DOI: 10.1055/s-0040-1706039

special topic

Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF₄Cl and Ar-SF₅ Synthesis

Lin Wang

,

Shengyang Ni

,

Josep Cornella ∗

Abstract

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Abstract

In this manuscript we describe the oxidative fluorination of aryl phosphorothiolates to access Ar-SF₄Cl compounds. These compounds serve as precursors for the highly coveted Ar-SF₅ compounds. The use of phosphorothiolates as starting materials permits access to Ar-SF₄Cl from a wide variety of available starting materials, namely boronic acids, diazonium salts, aryl iodides, thiophenols, or simple arenes. The protocol has been demonstrated for >10 examples and showed good tolerance to various functional groups. Finally, we demonstrated that AgBF₄ can be used as a fluorinating agent, affording good yields of an Ar-SF₅.

Key words

fluorine - phosphorus - sulfur - pentafluorosulfanylation - isosteres

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References

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