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Palladium on Charcoal Catalyzed 3,4-Hydroperoxidation of α-Substituted Enals with Triethylsilane and Water

Sakari Tuokko, Petri M. Pihko*

*Department of Chemistry and NanoScience Center, University of Jyväskylä, Survontie 9B, 40520 Jyväskylä, Finland, Email: petri.pihkojyu.fi

S. Tuokko, P. M. Pihko, Synlett, 2016, 27, 1649-1652.

DOI: 10.1055/s-0035-1561633 (free Supporting Information)


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Abstract

Aldehyde α-hydroperoxides can be accessed from α-substituted acroleins with triethylsilane and water under Pd/C catalysis and aerobic conditions via a Pd/C-catalyzed conjugate reduction step and a subsequent hydroperoxidation step. Upon reduction, 2,2-disubstituted 1,2-diols are obtained.

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Key Words

autoxidation, enols, palladium,  triethylsilane, oxygen, sodium borohydride, aldehydes, hydroperoxides, hydrosilylation, 1,2-diols


ID: J60-Y2016