Ruthenium-catalyzed oxidation of alkenes, alkynes, and alcohols to organic acids with aqueous hydrogen peroxide

Abstract

A protocol that adopts aqueous hydrogen peroxide as a terminal oxidant and [(Me 3tacn)(CF 3CO 2) 2Ru III(OH 2)]CF 3CO 2 (1; Me 3tacn = l,4,7-trimethyl-l,4,7-triazacyclononane) as a catalyst for oxidation of alkenes, alkynes, and alcohols to organic acids in over 80% yield is presented. For the oxidation of cyclohexene to adipic acid, the loading of 1 can be lowered to 0.1 mol%. On the one-mole scale, the oxidation of cyclohexene, cyclooctene, and 1-octanol with 1 mol% of 1 produced adipic acid (124g, 85% yield), suberic acid (158 g, 91% yield), and 1-octanoic acid (129 g, 90% yield), respectively. The oxidative C=C bondcleavage reaction proceeded through the formation of cis- and trans-diol intermediates, which were further oxidized to carboxylic acids via C-C bond cleavage. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.