Fluorobenziodoxole-BF3 reagent for Iodo(III)etherification of alkynes in ethereal solvent

Fluorobenziodoxole-BF3 reagent for Iodo(III)etherification of alkynes in ethereal solvent

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-al...

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Bibliographic Details
Main Authors: Chai, Jinkui, Ding, Wei, Wu, Junliang, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Biological sciences::Biochemistry
Alkynes
Lewis Acid
Online Access:https://hdl.handle.net/10356/155202
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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