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Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones

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Abstract

The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.

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The authors would like to acknowledge IFPE and CNPq (456523/2014-6) granting for financial support.

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  1. Departamento de Sistemas, Processos e Controles Industriais, Instituto Federal de Educação, Ciência e Tecnologia de Pernambuco, Cidade Universitária, Recife, PE, CEP 50740-540, Brazil

    Ayrlane Sales, Isabela Andrade de Oliveira e Castro, Frederico Duarte de Menezes, Thiago Matheus Guimarães Selva & Márcio Vilar

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Sales, A., de Oliveira e Castro, I.A., de Menezes, F.D. et al. Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones. J Incl Phenom Macrocycl Chem 95, 295–305 (2019). https://doi.org/10.1007/s10847-019-00944-4

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