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Title: Fluorobenziodoxole-BF3 reagent for Iodo(III)etherification of alkynes in ethereal solvent
Authors: Chai, Jinkui
Ding, Wei
Wu, Junliang
Yoshikai, Naohiko
Keywords: Science::Biological sciences::Biochemistry
Issue Date: 2020
Source: Chai, J., Ding, W., Wu, J. & Yoshikai, N. (2020). Fluorobenziodoxole-BF3 reagent for Iodo(III)etherification of alkynes in ethereal solvent. Chemistry - An Asian Journal, 15(14), 2166-2169.
Project: MOE2016-T2-2-043 
Journal: Chemistry - An Asian Journal 
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.
ISSN: 1861-4728
DOI: 10.1002/asia.202000653
Schools: School of Physical and Mathematical Sciences 
Rights: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA,Weinheim. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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