title: Ruthenium-catalyzed self-coupling of primary and secondary alcohols with the liberation of dihydrogen.
abstract: The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone dimers with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone.
authors.affiliation: Department of Chemistry, Technical University of Denmark, DK 2800 Lyngby, Denmark.
authors.forename: Ilya S
authors.initials: IS
authors.lastname: Makarov
authors.forename: Robert
authors.initials: R
authors.lastname: Madsen
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D000438:Alcohols; D007659:Ketones; D009942:Organometallic Compounds; D012428:Ruthenium; D006859:Hydrogen