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The Role Ionic Liquid [BMIM][PF<sub>6</sub>] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction
oleh: Poliane K. Batista, João Marcos G. de O. Ferreira, Fabio P. L. Silva, Mario L. A. A Vasconcellos, Juliana A. Vale
Format: | Article |
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Diterbitkan: | MDPI AG 2019-05-01 |
Deskripsi
Tetrahydropyran (THP) rings are common in several natural products, therefore, various strategies are being developed to synthesize these rings. The present work described the study of a one-pot synthesis of 2,4,6-trisubstituted tetrahydropyran compounds promoted by the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF<sub>6</sub>] through a Barbier−Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF<sub>6</sub>] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF<sub>6</sub>-, accelerates the Barbier reaction when used alone, and the excess SnBr<sub>2</sub> from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic liquid can be recovered and reused five times in the preparation of 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran without significant yield loss.