title: Nitroxyl radical/PhI(OAc)2: one-pot oxidative cleavage of vicinal diols to (di)carboxylic acids.
abstract: A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)(2) is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. m-shibu@ps.nagoya-u.ac.jp
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Shibuya
authors.forename: Takuro
authors.initials: T
authors.lastname: Shibuta
authors.forename: Hayato
authors.initials: H
authors.lastname: Fukuda
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D005609:Free Radicals / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011744:Pyrimidinones / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D005609:Free Radicals; D005960:Glucosides; D007462:Iodobenzenes; D009589:Nitrogen Oxides; D011744:Pyrimidinones; C009661:vicine; C039900:nitroxyl