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

J Org Chem

Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi Saga 840-8502, Japan.

Published: March 2018

The reaction of alkynes with PhIO and Py·HF followed by treatment with BF·OEt 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 ArIF.

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http://dx.doi.org/10.1021/acs.joc.7b03223DOI Listing

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