Bench-stable reagents for modular access to persulfuranyl scaffolds

Renzhe Li, Chang Liu, Chao Hu, Jet Tsien, Michael Hayes, Si-Jie Chen, Yuzuru Kanda, Rohan R. Merchant, Bryan S. Matsuura and Tian Qin ()
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Renzhe Li: The University of Texas Southwestern Medical Center, Department of Biochemistry
Chang Liu: The University of Texas Southwestern Medical Center, Department of Biochemistry
Chao Hu: The University of Texas Southwestern Medical Center, Department of Biochemistry
Jet Tsien: The University of Texas Southwestern Medical Center, Department of Biochemistry
Michael Hayes: Merck & Co., Inc., Department of Discovery Chemistry
Si-Jie Chen: Merck & Co., Inc., Department of Discovery Chemistry
Yuzuru Kanda: Novartis Biomedical Research
Rohan R. Merchant: Merck & Co., Inc., Department of Discovery Chemistry
Bryan S. Matsuura: Merck & Co., Inc., Department of Discovery Chemistry
Tian Qin: The University of Texas Southwestern Medical Center, Department of Biochemistry

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract Pentafluorosulfanyl group has been long considered a potential (bio)isostere for tert-butyl and trifluoromethyl groups, yet limitations in methodologies have constrained access to it. To bridge this gap, we have developed a general pentafluorosulfanylation platform that employs bench-stable solid reagents to generate SF5 radicals via a decarboxylation and β-scission sequence. This strategy enables a variety of operationally simple transformations, expanding the accessibility of SF5-containing molecules. Notably, this reagent design is also adaptable to other persulfuranyl groups, such as trifluoromethyl tetrafluorosulfanyl and aryl tetrafluorosulfanyl groups. Taken together, generating a collection of these stable reagents and practitioner-friendly chemical methodologies enables the synthesis of challenging and biologically relevant sulfur(VI) chemical entities in an expedient manner.

Date: 2025
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DOI: 10.1038/s41467-025-63621-w

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