Fluorobenziodoxole−BF3 Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent

Jinkui Chai, Wei Ding, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A combination of fluorobenziodoxole (FBX) and BF3 ⋅ OEt2 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 BF3, followed by electrophilic activation of the alkyne by the resulting cationic IIII species that triggers the nucleophilic addition of the ethereal oxygen.

Original languageEnglish
Pages (from-to)2166-2169
Number of pages4
JournalChemistry - An Asian Journal
Volume15
Issue number14
DOIs
Publication statusPublished - 2020 Jul 16
Externally publishedYes

Keywords

  • Lewis acid
  • alkynes
  • halofunctionalization
  • hypervalent iodine compounds
  • vinyl ethers

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Fluorobenziodoxole−BF<sub>3</sub> Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent'. Together they form a unique fingerprint.

Cite this