2002 oxidation, dehydrogenation

oxidation, dehydrogenationO 0212

36 - 049Practical Os/Cu-Cocatalyzed Air Oxidation of Allyl and BenzylAlcohols at Room Temperature and Atmospheric Pressure. —A new efficient and chemoselective oxidation of benzylic and allylic alcoholsto the corresponding carbonyl compounds is presented, involving an osmiumtetroxide–quinuclidine–allyl ether complex and copper(II) cocatalyst with air atroom temperature and normal pressure. The method tolerates easily oxidizedfunctional groups like sulfide or double bonds as well as acid labile groupslike acetals. No overoxidation to the corresponding acids is observed. Simplealiphatic primary and secondary alcohols are not oxidized, only the presence ofelectron-withdrawing groups or cyclopropyl group allows some oxidation to takeplace [cf. (VIII)]. — (MULDOON, JOHN; BROWN, SETH N.; Org. Lett. 4(2002) 6, 1043-1045; Dep. Chem. Biochem., Univ. Notre Dame, Notre Dame,IN 46556, USA; EN)

1