Radical Trifluoromethyl- and Perfluoroalkylation via Reductive and Oxidative Processes

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In the second project period new fluorinated Togni-type I(III)-reagents will be developed and used as C-radical precursors for the mild introduction of functionalized fluorinated alkyl groups into various pi-systems (alkenes, arenes and alkynes). Reactions will be mediated by mild organic single electron reductants such as TEMPONa. In addition, organic dianions will be tested as single electron transfer reducing reagents for clean C-radical generation in the reaction with I(III)-reagents. Cross-coupling of longer-lived radical anions with short-lived perfluoroalkyl radicals will be investigated. In these processes the concept of the Persistent Radical Effect will be applied. In addition, a method for phenol O-trifluoromethylation, which is an unsolved problem in synthesis, will be developed. Finally, oxidative radical trifluoromethylation and trifluoromethylthiolation will be explored.