Amino acid ionic liquids as catalysts in a solvent-free Morita–Baylis–Hillman reaction. Issue 42 (2nd July 2018)

• Record Type: Journal Article
• Authors: Pereira, Mathias Prado; Souza Martins, Rafaela de; de Oliveira, Marcone Augusto Leal; Bombonato, Fernanda Irene
• Is Part Of: RSC advances. Volume 8:Issue 42(2018)
• Page Start: 23903
• Page End: 23913
• Publication Date: 2018-07-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8ra02409j
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : In this work, we describe the preparation of ten amino acid ionic liquids (AAILs). The AAILs were used as catalysts in a Morita–Baylis–Hillman (MBH) reaction. The MBH adducts were obtained from moderate to good yields and in their racemic form. Abstract : In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita–Baylis–Hillman (MBH) reaction. The ionic liquids derivative froml -proline andl -histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives froml -valine, l -leucine, andl -tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.