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Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

dc.contributor.authorJi, Tengfei
dc.contributor.authorChen, Xiang-Yu
dc.contributor.authorHuang, Long
dc.contributor.authorRueping, Magnus
dc.date.accessioned2020-03-18T12:35:08Z
dc.date.available2020-03-18T12:35:08Z
dc.date.issued2020-03-16
dc.identifier.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
dc.identifier.doi10.1021/acs.orglett.0c00493
dc.identifier.urihttp://hdl.handle.net/10754/662195
dc.description.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.
dc.description.sponsorshipThe 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).
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acs.orglett.0c00493
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.0c00493.
dc.titleRemote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalOrganic Letters
dc.rights.embargodate2021-03-16
dc.eprint.versionPost-print
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
kaust.personRueping, Magnus
refterms.dateFOA2020-03-19T10:19:20Z
dc.date.published-online2020-03-16
dc.date.published-print2020-04-03


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