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Radical Addition of Silanes to Alkenes Followed by Oxidation

Matthew J. Palframan, Andrew F. Parsons*, Paul Johnson

*Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK, Email: andy.parsonsyork.ac.uk

M. J. Palframan, A. F. Parsons, P. Johnson, Synlett, 2011, 2811-2814.

DOI: 10.1055/s-0031-1289568



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Abstract

Using triethylborane as the initiator, phenyldimethylsilane and trichlorosilane undergo efficient radical hydrosilylation reactions with various alkenes. Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in moderate yields. This two-step process leads to the anti-Markovnikov hydration of alkenes.

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Key Words

addition reaction, alcohols, alkenes, radical reaction, alkyl silanes


ID: J60-Y2011-3410