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Addition of activated olefins to cyclic N-acyliminium ions in ionic liquids
Authors:Ronaldo Aloise Pilli  Luís Gustavo Robello  Jairton Dupont  Alexandre Augusto Moreira Lapis  Brenno A da Silveira Neto
Institution:a Institute of Chemistry, State University of Campinas—UNICAMP, 13083-970, Campinas, SP, Brazil
b Laboratory of Molecular Catalysis, Institute of Chemistry—UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre, 91501-970, RS, Brazil
Abstract:Organoindate(III) ionic liquid (BMI·InCl4) was successfully employed in the nucleophilic addition of allyltrimethylsilane, silyl enol ethers and ketene silyl acetals to in situ generated cyclic N-acyliminium ions at room temperature without the need of an external Lewis acid. The corresponding α-substituted heterocycles were obtained in good yields and the recovered ionic liquid phase could be reused at least three times.
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