The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier-Prins Reaction.

ABSTRACT: 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][PF6] through a Barbier-Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF6] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF6-, accelerates the Barbier reaction when used alone, and the excess SnBr2 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 i

SUBMITTER: Batista PK 

PROVIDER: S-EPMC6600659 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature