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C-O Hydrogenolysis Catalyzed by Pd-PMHS Nanoparticles in the Company of Chloroarenes

Ronald J. Rahaim, Jr. and Robert E. Maleczka, Jr.*

*Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, United States, Email: maleczkachemistry.msu.edu

R. J. Rahaim, Jr., R. E. Maleczka, Jr., Org. Lett., 2011, 13, 584-587.

DOI: 10.1021/ol102757v (free Supporting Information)


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Abstract

Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS) effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates in the presence of aqueous KF and a catalytic amount of an aromatic chloride involving palladium-nanoparticle-catalyzed hydrosilylation followed by C-O reduction. The chloroarene facilitates the hydrogenolysis through the slow controlled release of HCl.

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Key Words

PMHS, Deoxygenations


ID: J54-Y2011-0300