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Fluorobenziodoxole−BF 3 Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent
Author(s) -
Chai Jinkui,
Ding Wei,
Wu Junliang,
Yoshikai Naohiko
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000653
Subject(s) - electrophile , cationic polymerization , nucleophile , chemistry , reagent , alkyne , stereoselectivity , ether , solvent , bond cleavage , cleavage (geology) , medicinal chemistry , organic chemistry , combinatorial chemistry , polymer chemistry , catalysis , materials science , fracture (geology) , composite material
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.