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Ionic Liquids Promoted the C-Acylation of Acetals in Solvent-free Conditions

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Abstract

The synthesis of a series of fourteen 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (2,3) [CX3COC(R2)=C(R1)OMe, where X = Cl, F; R1/R2 = Me/H, Bu/H, i-Bu/H, Ph/H, Thien-2-yl/H, –(CH2)4–, –CH(CH2)4CH(CH2)2–] from the acylation reactions of acetals (1) with trichloroacetyl chloride or trifluoroacetic anhydride in the presence of equimolar amounts of pyridine and imidazolium based ionic liquid ([BMIM][BF4] or [BMIM][PF6]) is reported. The reaction time, yields and IL recyclation are also investigated and this method showed advantages over the methods described in the literature.

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Acknowledgments

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Contracts No. 46.0804/00-6 and 480067/01-5), Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) and CAPES for financial support and fellowships.

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Authors and Affiliations

  1. Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97.105-900, Brazil

    Marcos A. P. Martins, Emerson A. Guarda, Clarissa P. Frizzo, Dayse N. Moreira, Mara R. B. Marzari, Nilo Zanatta & Helio G. Bonacorso

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  1. Marcos A. P. Martins
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  2. Emerson A. Guarda
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  3. Clarissa P. Frizzo
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  4. Dayse N. Moreira
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  5. Mara R. B. Marzari
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  6. Nilo Zanatta
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  7. Helio G. Bonacorso
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Correspondence to Marcos A. P. Martins.

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Martins, M.A.P., Guarda, E.A., Frizzo, C.P. et al. Ionic Liquids Promoted the C-Acylation of Acetals in Solvent-free Conditions. Catal Lett 130, 93–99 (2009). https://doi.org/10.1007/s10562-009-9873-6

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  • DOI: https://doi.org/10.1007/s10562-009-9873-6

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