Oxidation

Huanfeng Jiang at the South China University of Technology developed (J. Am. Chem. Soc. 2013, 135, 5286) the palladium-catalyzed dehydrogenative aminohalogenation of methyl acrylate with aniline 1. A 1,3-hydrogen shift/ chlorination catalyzed by an iridium complex was reported (Angew. Chem. Int. Ed. 2013, 52, 6273) by Belén Martín- Matute at Stockholm University. Robert M. Waymouth discovered (J. Am. Chem. Soc. 2013, 135, 7593) the chemoselective oxidation of polyol 5 by a cationic palladium species. A ruthenium(II) hydride was found to catalyze the conversion of alcohols such as 7 to carboxylic acids using water as the oxygen source as disclosed (Nature Chem. 2013, 5, 122) by David Milstein at the Weizmann Institute of Science in Israel. Susan K. Hanson at the Los Alamos National Laboratory in New Mexico reported (Org. Lett. 2013, 15, 650) the acceptorless dehydrogenation of alcohols catalyzed by cobalt complex 12 to form imines such as 13 upon reaction with an amine. A collabo­ration led by Pedro J. Pérez at the University of Huelva in Spain studied (J. Am. Chem. Soc. 2013, 135, 3887) the oxidation of alkanes under catalysis with copper complex 15, primarily yielding alcohols and ketones, such as in the conversion of cyclohexane (14) to cyclohexanol (16) and cyclohexanone (17). A remarkable symmetry-breaking Wacker oxidation of diene 18 to produce 19 was the key step in the total synthesis of (+)-obolactone reported (Org. Lett. 2013, 15, 1294) by Reinhard Brückner at the University of Freiburg in Germany. Kiyotomi Kaneda at the University of Osaka found (Angew. Chem. Int. Ed. 2013, 52, 5961) that a palladium salt catalyzes the conversion of electron-deficient internal olefin 20 to ketone 21. As part of a program to develop environmentally sustainable procedures, Caterina Fusco at the University of Bari in Italy described (Tetrahedron Lett. 2013, 54, 515) the oxidative cleavage of lactam 22 by methyl(trifluoromethyl)dioxirane in water to pro­duce ω-nitro acid 24. Motomu Kanai at the University of Tokyo reported (Org. Lett. 2013, 15, 1918) the β-functionalization of tertiary aromatic amine 25 with nitroolefin 26 to produce 27 by iron catalysis.