ortho-Selective phenol-coupling reaction by anodic treatment on boron-doped diamond electrode using fluorinated alcohols.
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.
Kirste
Axel
A
Rheinische Friedrich-Wilhelms-Universität Bonn, Kekulé-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany.
Nieger
Martin
M
Malkowsky
Itamar M
IM
Stecker
Florian
F
Fischer
Andreas
A
Waldvogel
Siegfried R
SR
D000438:Alcohols / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D018130:Diamond / Q000737:chemistry*; D004563:Electrochemistry / Q000295:instrumentation / Q000379:methods; D004566:Electrodes; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry
D000438:Alcohols; D006845:Hydrocarbons, Fluorinated; D010636:Phenols; D020005:Propanols; C001337:hexafluoroisopropanol; D018130:Diamond; D001895:Boron