Fluorobenziodoxole−BF<sub>3</sub> Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent
Jinkui Chai, Wei Ding, Junliang Wu, Naohiko Yoshikai
Abstract
Abstract A combination of fluorobenziodoxole (FBX) and BF 3 ⋅ OEt 2 in cyclopentyl methyl ether promotes regio‐ and stereoselective addition of benziodoxole and methoxy groups to alkynes. This difunctionalization reaction tolerates a variety of functionalized internal and terminal alkynes to afford trans ‐β‐alkoxyvinylbenziodoxoles, which represent versatile precursors to stereochemically well‐defined multisubstituted vinyl ethers. The reaction is proposed to involve cleavage of the I−F bond of FBX by BF 3 , followed by electrophilic activation of the alkyne by the resulting cationic I III species that triggers the nucleophilic addition of the ethereal oxygen.
Topics & Concepts
ElectrophileCationic polymerizationNucleophileReagentChemistryAlkyneStereoselectivityEtherSolventCleavage (geology)Bond cleavageMedicinal chemistryVinyl etherOrganic chemistryCombinatorial chemistryCatalysisMaterials scienceCopolymerPolymerComposite materialFracture (geology)Oxidative Organic Chemistry ReactionsVanadium and Halogenation ChemistryRadical Photochemical Reactions