title: Synthesis of phenols via fluoride-free oxidation of arylsilanes and arylmethoxysilanes.
abstract: Rapid, efficient methods have been developed to prepare phenols from the oxidation of arylhydrosilanes. The effects of arene substituents and fluoride promoters on this process show that while electron-deficient arenes can undergo direct oxidation from the hydrosilane, electron-rich aromatics benefit from silane activation via oxidation to the methoxysilane using homogeneous or heterogeneous transition metal catalysis. The combination of these two oxidations into a streamlined flow procedure involving minimal processing of reaction intermediates is also reported.
authors.affiliation: Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Elizabeth J
authors.initials: EJ
authors.lastname: Rayment
authors.forename: Nick
authors.initials: N
authors.lastname: Summerhill
authors.forename: Edward A
authors.initials: EA
authors.lastname: Anderson
mesh_terms: D002384:Catalysis; D004583:Electrons; D005459:Fluorides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010636:Phenols; D012821:Silanes; D005459:Fluorides