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Synthesis of Phenols via Fluoride-free Oxidation of Arylsilanes and Arylmethoxysilanes

Elizabeth J. Rayment, Nick Summerhill and Edward A. Anderson*

*Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom, Email: edward.andersonchem.ox.ac.uk

E. J. Rayment, N. Summerhill, E. A. Anderson, J. Org. Chem., 2012, 77, 7052-7060.

DOI: 10.1021/jo301363h (free Supporting Information)



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Abstract

Rapid, efficient methods enable the preparation of phenols from the oxidation of arylhydrosilanes. Electron-rich aromatics benefit from silane activation via oxidation to the methoxysilane using homogeneous or heterogeneous transition metal catalysis. A combination of these two oxidations into a streamlined flow procedure involves minimal processing of reaction intermediates.

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Key Words

Silanes, Phenols, Hydrogen Peroxide


ID: J42-Y2012-2660