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RESEARCH PRODUCT
Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol
Johannes L. RöcklAnton WiebeTile GieshoffYasushi ImadaYasushi ImadaDieter SchollmeyerSiegfried R. WaldvogelRobert FrankeKazuhiro Chibasubject
Green chemistryChemical transformation010405 organic chemistryChemistryArylGeneral Chemistry010402 general chemistryElectrochemistry01 natural sciencesCombinatorial chemistryCatalysis0104 chemical sciencesMetalchemistry.chemical_compoundNucleophileReagentvisual_artvisual_art.visual_art_mediumSurface modificationdescription
A selective dehydrogenative electrochemical functionalization of benzylic positions that employs 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) has been developed. The electrogenerated products are versatile intermediates for subsequent functionalizations as they act as masked benzylic cations that can be easily activated. Herein, we report a sustainable, scalable, and reagent- and metal-free dehydrogenative formal benzyl-aryl cross-coupling. Liberation of the benzylic cation was accomplished through the use of acid. Valuable diarylmethanes are accessible in the presence of aromatic nucleophiles. The direct application of electricity enables a safe and environmentally benign chemical transformation as oxidizers are replaced by electrons. A broad variety of different substrates and nucleophiles can be employed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-04-29 | Angewandte Chemie International Edition |