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New copper(II) catalytic systems for the mild oxidative C–H functionalization of cycloalkanes and cycloalkenes were developed, which are based on a series of mixed-ligand aminoalcohol-dicarboxylate coordination polymers, namely [Cu 2 (μ-dmea) 2 (μ-nda)(H 2 O) 2 ] n ·2nH 2 O ( 1 ), [Cu 2 (μ-Hmdea) 2 (μ-nda)] n ·2nH 2 O ( 2 ), and [Cu 2 (μ-Hbdea) 2 (μ-nda)] n ·2nH 2 O ( 3 ) that bear slightly different dicopper(II) aminoalcoholate cores, as well as on a structurally distinct dicopper(II) [Cu 2 (H 4 etda) 2 (μ-nda)]·nda·4H 2 O ( 4 ) derivative [ abbreviations : H 2 nda, 2,6-naphthalenedicarboxylic acid; Hdmea,  N,N′ -dimethylethanolamine; H 2 mdea,  N -methyldiethanolamine; H 2 bdea,  N -butyldiethanolamine; H 4 etda,  N,N,N′,N′ -tetrakis(2-hydroxyethyl)ethylenediamine]. Compounds  1 – 4  act as homogeneous catalysts in the three types of model catalytic reactions that proceed in aqueous acetonitrile medium under mild conditions (50–60°C): (i) the oxidation of cyclohexane by hydrogen peroxide to cyclohexyl hydroperoxide, cyclohexanol, and cyclohexanone, (ii) the oxidation of cycloalkenes (cyclohexene, cyclooctene) by hydrogen peroxide to a mixture of different oxidation products, and (iii) the single-pot hydrocarboxylation of cycloalkanes (cyclopentane, cyclohexane, cycloheptane, cyclooctane) by carbon monoxide, water, and a peroxodisulfate oxidant into the corresponding cycloalkanecarboxylic acids. The catalyst and substrate scope as well as some mechanistic features were investigated; the highest catalytic activity of  1 – 4  was observed in the hydrocarboxylation of cycloalkanes, allowing to achieve up to 50% total product yields (based on substrate).

pure and applied chemistry

Mixed-ligand aminoalcohol-dicarboxylate copper(II) coordination polymers as catalysts for the oxidative functionalization of cyclic alkanes and alkenes