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Groebke-Blackburn-Bienaymé Multicomponent Reaction Catalysed by Reusable Brϕnsted-Acidic Ionic Liquids

Anjos, Nicolas Santos; Chapina, Agáta Ishiba; Santos, Ana Rute; Licence, Peter; Longo Junior, Luiz Sidney

Groebke-Blackburn-Bienaymé Multicomponent Reaction Catalysed by Reusable Brϕnsted-Acidic Ionic Liquids Thumbnail


Authors

Nicolas Santos Anjos

Agáta Ishiba Chapina

Ana Rute Santos

Luiz Sidney Longo Junior



Abstract

In the present work, the use of Brϕnsted acidic ionic liquids (BAIL) as catalysts for Groebke-Blackburn-Bienaymé (GBB) multicomponent reactions was systematically investigated. A series of four 1-(butyl-4-sulfonic)-3-methylimidazolium salts bearing different anions was easily prepared and screened as acidic catalysts for this transformation. The best reaction conditions were stablished as 20 mol % of catalyst [(SO3H)4C4C1Im][OTf] in refluxing EtOH or MeOH under conventional heating and in sealed tube at 150 °C for 1–4 hours under microwave heating, affording a series of imidazo-fused heterocycles in moderate to excellent yields (42–93 %). The homogeneous BAIL catalyst could be recycled and reused in four consecutive reaction cycles, despite of a laborious recovery procedure employed. This approach represents the first example of a task-specific reusable homogeneous Brϕnsted acidic catalyst in GBB reactions and opens new opportunities for the exploration of acidic ionic liquid phases as catalysts for this fascinating multicomponent reaction.

Citation

Anjos, N. S., Chapina, A. I., Santos, A. R., Licence, P., & Longo Junior, L. S. (2022). Groebke-Blackburn-Bienaymé Multicomponent Reaction Catalysed by Reusable Brϕnsted-Acidic Ionic Liquids. European Journal of Organic Chemistry, 2022(40), Article e202200615. https://doi.org/10.1002/ejoc.202200615

Journal Article Type Article
Acceptance Date Sep 1, 2022
Online Publication Date Sep 4, 2022
Publication Date Oct 26, 2022
Deposit Date Sep 26, 2022
Publicly Available Date Sep 5, 2023
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2022
Issue 40
Article Number e202200615
DOI https://doi.org/10.1002/ejoc.202200615
Keywords Organic Chemistry; Physical and Theoretical Chemistry
Public URL https://nottingham-repository.worktribe.com/output/11461897
Publisher URL https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202200615
Additional Information Received: 2022-05-28; Accepted: 2022-09-01; Published: 2022-09-04

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