Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

Tengfei Ji, Xiang-Yu Chen, Long Huang, Magnus Rueping

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33 Scopus citations


The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)–SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C–C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.
Original languageEnglish (US)
JournalOrganic Letters
StatePublished - Mar 16 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement No. 617044 (SunCatChem).


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