An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and Catalytic OsO4

Abstract

(Figure Presented) PhI(OAc)2 In the presence of OsO4 (cat.) and 2,6-lutidine cleaves oleflnlc bonds to yield the corresponding carbonyl compounds, albeit, In some cases, with a-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO4 (cat.), 2,6-lutidine, and PhI(OAc) 2. © 2010 American Chemical Society.