Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage
KAUST DepartmentChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2020-03-16
Print Publication Date2020-04-03
Embargo End Date2021-03-16
Permanent link to this recordhttp://hdl.handle.net/10754/662195
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AbstractThe 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.
CitationJi, T., Chen, X.-Y., Huang, L., & Rueping, M. (2020). Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage. Organic Letters. doi:10.1021/acs.orglett.0c00493
SponsorsThe 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).
PublisherAmerican Chemical Society (ACS)