<i>gem</i>-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu<sub>4</sub>NBF<sub>4</sub> or electrogenerated acid

<i>gem</i>-Difluorination of carbon-carbon triple bonds was conducted using Brønsted acids, such as Tf<sub>2</sub>NH and TfOH, combined with Bu<sub>4</sub>NBF<sub>4</sub> as the fluorine source. The electrochemical oxidation of a Bu<sub>4</sub>NBF<sub>4</sub>/CH<sub>2</sub>Cl<sub>2</sub> solution containing alkyne substrates could also give the corresponding <i>gem</i>-difluorinated compounds (<i>in-cell</i> method). The <i>ex-cell</i> electrolysis method was also applicable for <i>gem</i>-difluorination of alkynes.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2024-09-06
DOI
https://doi.org/10.3762/bjoc.20.194
Citations
5
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.04

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article

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu4NBF4 or electrogenerated acid

Hiroki Shimao, Keiji Nishiwaki, Kengo Hamasaki, Kouichi Matsumoto et al.
5 citations
Beilstein Journal of Organic Chemistry
Fluorine in Organic Chemistry
1.04
article

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu4NBF4 or electrogenerated acid

Hiroki Shimao, Keiji Nishiwaki, Kengo Hamasaki, Kouichi Matsumoto, Mizuki Yamaguchi, Shigenori Kashimura
article en
5 citations

Abstract

<i>gem</i>-Difluorination of carbon-carbon triple bonds was conducted using Brønsted acids, such as Tf<sub>2</sub>NH and TfOH, combined with Bu<sub>4</sub>NBF<sub>4</sub> as the fluorine source. The electrochemical oxidation of a Bu<sub>4</sub>NBF<sub>4</sub>/CH<sub>2</sub>Cl<sub>2</sub> solution containing alkyne substrates could also give the corresponding <i>gem</i>-difluorinated compounds (<i>in-cell</i> method). The <i>ex-cell</i> electrolysis method was also applicable for <i>gem</i>-difluorination of alkynes.

Beilstein Journal of Organic ChemistryVol. 20
Kindai University (JP)
Kindai University, Kanazawa University, Japan Society for the Promotion of Science
Openalex Percentile: Top 27%
Fluorine in Organic Chemistry
1.04
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