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Synthesis 2021; 53(22): 4308-4312
DOI: 10.1055/s-0040-1706039
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
Financial support for this work was provided by the Max-Planck-Gesellschaft, the Max-Planck-Institut für Kohlenforschung, and the Fonds der Chemischen Industrie (VCI). This work was also supported by an Exploration Grant of the Boehringer Ingelheim Foundation (BIS).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706039.
- Supporting Information
Publication History
Received: 16 April 2021
Accepted: 19 April 2021
Article published online:
20 May 2021
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