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• W2289346722 abstract "Abstract The radical trifluoromethylation of thiophenol in condensed phase applying reagent 1 (3,3‐dimethyl‐1‐(trifluoromethyl)‐1 λ 3 ,2‐benziodoxol) has been examined by both theoretical and experimental methodologies. On the basis of ab initio molecular dynamics and metadynamics we show that radical reaction mechanisms favourably compete with polar ones involving the S ‐centred nucleophile thiophenol, their free energies of activation, Δ F ≠ , lying between 9 and 15 kcal mol −1 . We further show that the origin of the proton activating the reagent is important. Hammett plot analysis reveals intramolecular protonation of 1 , thus generating negative charge on the sulfur atom in the rate‐determining step. The formation of a CF 3 radical can be thermally induced by internal dissociative electron transfer, its activation energy, Δ F ≠ , amounting to as little as 10.8 and 2.8 kcal mol −1 for reagent 1 and its protonated form 2 , respectively. The reduction of the iodine atom by thiophenol occurs either subsequently or in a concerted fashion." @default.
• W2289346722 created "2016-06-24" @default.
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• W2289346722 date "2016-01-07" @default.
• W2289346722 modified "2023-10-16" @default.
• W2289346722 title "<i>S</i>-Trifluoromethylation of Thiols by Hypervalent Iodine Reagents: A Joint Experimental and Computational Study" @default.
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• W2289346722 doi "https://doi.org/10.1002/chem.201503774" @default.
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