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

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journal contribution
posted on 18.02.2011, 00:00 by Ronald J. Rahaim, Robert E. Maleczka
Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS), in conjunction with aqueous KF, and a catalytic amount of an aromatic chloride, effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates at room temperature in THF. Preliminary mechanistic experiments suggest the process to involve palladium−nanoparticle-catalyzed hydrosilylation followed by C−O reduction. The chloroarene additive appears to facilitate the hydrogenolysis process through the slow controlled release of HCl.