ortho-Selective Phenol-Coupling Reaction by Anodic Treatment on Boron-Doped Diamond Electrode Using Fluorinated Alcohols

• Published in: Chemistry : a European journal Vol. 15; no. 10; pp. 2273 - 2277
• Main Authors: Kirste, Axel, Nieger, Martin, Malkowsky, Itamar M., Stecker, Florian, Fischer, Andreas, Waldvogel, Siegfried R.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 23.02.2009; WILEY‐VCH Verlag; Wiley
• Subjects: Alcohols - chemistry; Boron - chemistry; Chemistry; Chemistry, Multidisciplinary; CC coupling; Diamond - chemistry; electrochemistry; Electrochemistry - instrumentation; Electrochemistry - methods; Electrodes; fluorine; Hydrocarbons, Fluorinated - chemistry; Models, Molecular; oxidation; Oxidation-Reduction; phenols; Phenols - chemical synthesis; Phenols - chemistry; Physical Sciences; Propanols - chemistry; Science & Technology; C-C coupling; phenols; electrochemistry; ASYMMETRIC CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; MOLYBDENUM; oxidation; LIGANDS; SOLVENTS; CONSTRUCTION; ENONES; METATHESIS; fluorine
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200802556

Enlarged scope by fluorinated mediators: Oxyl radicals are easily formed on boron‐doped diamond (BDD) electrodes and can be exploited for the ortho‐selective coupling to the corresponding biphenols (see scheme). At partial conversion, a clean transformation is achieved that can be applied to electron‐rich as well as fluorinated phenols. Enlarged scope by fluorinated mediators: Oxyl radicals are easily formed on boron‐doped diamond (BDD) electrodes and can be exploited for the ortho‐selective coupling to the corresponding biphenols (see scheme). At partial conversion, a clean transformation is achieved that can be applied to electron‐rich as well as fluorinated phenols.