Synthesis of β‑Fluorovinyliodonium Salts by the Reaction of Alkynes with Hypervalent Iodine/HF Reagents

The reaction of alkynes with PhIO and Py·HF followed by treatment with BF3·OEt2 gave β-fluorovinyliodonium tetrafluoroborates in good to high yields. More conveniently, the reaction using PhI and Py·HF in the presence of m-CPBA also afforded β-fluorovinyliodonium tetrafluoroborates in good yields. T...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-03, Vol.83 (5), p.2773-2778
Main Authors: Kitamura, Tsugio, Mizuno, Shota, Muta, Kensuke, Oyamada, Juzo
Format: Article
Language:English
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Summary:The reaction of alkynes with PhIO and Py·HF followed by treatment with BF3·OEt2 gave β-fluorovinyliodonium tetrafluoroborates in good to high yields. More conveniently, the reaction using PhI and Py·HF in the presence of m-CPBA also afforded β-fluorovinyliodonium tetrafluoroborates in good yields. These methods have the advantages that β-fluorovinyliodonium salts can be prepared without ArIF2.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b03223