Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage
Tengfei Ji, Xiang‐Yu Chen, Long Huang, Magnus Rueping
Abstract
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.
Topics & Concepts
ChemistryCleavage (geology)Bond cleavageStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisComposite materialFracture (geology)Materials scienceFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques