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Issue 96, 2014
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An efficient approach to the ammoxidation of alcohols to nitriles and the aerobic oxidation of alcohols to aldehydes in water using Cu(II)/pypzacac complexes as catalysts

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Abstract

Reactions of 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid (pypzacacH) ligand with Cu(OAc)2, Cu(NO3)2, CuSO4, Cu(ClO4)2 or CuCl2 produced four dinuclear Cu(II) complexes [{(MeOH)Cu(OAc)}(μ-κ21-pypzacac)]2·0.5H2O (1·0.5H2O), [{Cu(pypzacac)}(μ-κ21-pypzacac)2{Cu(H2O)2}](NO3)·2(MeOH)0.5·6H2O (2·2(MeOH)0.5·6H2O), [{(MeOH)Cu(mpypzacac)}(μ-SO4)]2·2MeOH (3·2MeOH; mpypzacac = methyl 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetate), [{Cu(mpypzacac)2}(μ-κ21-pypzacac){Cu(mpypzacac)}](ClO4)3·MeOH (4·MeOH) and one polymeric Cu(II) complex [(CuCl)(μ-κ31-pypzacac)]n (5), respectively. The mpypzacac ligand in 3 and 4 was in situ generated via the Cu2+-catalyzed dehydrative esterification of acetic acid of the pypzacacH ligand. Complexes 1–5 are characterized by elemental analysis, IR and single-crystal X-ray diffraction. Complex 1 contains two {(MeOH)Cu(OAc)} fragments that are interconnected by two μ-κ21-pypzacac ligands, forming a dimeric structure. In 2, {Cu(pypzacac)} and {Cu(H2O)2} units are bridged by a pair of μ-κ21-pypzacac ligands. In 3, two {Cu(mpypzacac)} fragments are linked by two μ-κ11-SO42− ions to form a dinuclear structure. Complex 4 also adopts a dimeric structure in which {Cu(mpypzacac)2} and {Cu(mpypzacac)} units are interconnected by one μ-κ31-pypzacac ligand. Complex 5 contains a 1D chain in which (CuCl) fragments are interlinked by μ-κ31-pypzacac ligands. Complexes 1–5 exhibited excellent catalytic performance in the ammoxidation of alcohol to nitrile and the aerobic oxidation of alcohol to aldehyde in water. The catalytic aqueous solution was easily separated and could be reused for several cycles without any obvious decay of catalytic efficiency.

Graphical abstract: An efficient approach to the ammoxidation of alcohols to nitriles and the aerobic oxidation of alcohols to aldehydes in water using Cu(ii)/pypzacac complexes as catalysts

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Publication details

The article was received on 02 Sep 2014, accepted on 10 Oct 2014 and first published on 10 Oct 2014


Article type: Paper
DOI: 10.1039/C4RA11743C
Citation: RSC Adv., 2014,4, 54007-54017
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    An efficient approach to the ammoxidation of alcohols to nitriles and the aerobic oxidation of alcohols to aldehydes in water using Cu(II)/pypzacac complexes as catalysts

    J. Xie, J. Bao, H. Li, D. Tan, H. Li and J. Lang, RSC Adv., 2014, 4, 54007
    DOI: 10.1039/C4RA11743C

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