Ring-Closing Metathesis for Fluoroolefins Using Ruthenium Catalysts with Six-Membered NHC Ligands

Although olefin metathesis is a superior method for the construction of olefins, the synthesis of fluoroolefins remains challenging. In this study, we report the exploration of ruthenium catalysts suitable for the ring-closing metathesis of fluoroolefins. Using ruthenium catalysts with appropriate six-membered N-heterocyclic carbene ligands, we successfully synthesized various five- and six-membered fluorinated ring olefins. DFT calculations suggested that the strong electron-donating properties and moderate bulkiness of the N-heterocyclic carbene ligands played crucial roles.

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Publication Details

Journal
Organic Letters
Published
2025-02-03
DOI
https://doi.org/10.1021/acs.orglett.4c04846
Citations
3
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
2.81
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article

Ring-Closing Metathesis for Fluoroolefins Using Ruthenium Catalysts with Six-Membered NHC Ligands

Shinsuke Inagi, Tatsuya Ueji, Ryu Tadano, Munenori Inoue
3 citations
Organic Letters
Synthetic Organic Chemistry Methods
2.81
article

Ring-Closing Metathesis for Fluoroolefins Using Ruthenium Catalysts with Six-Membered NHC Ligands

Shinsuke Inagi, Tatsuya Ueji, Ryu Tadano, Munenori Inoue
article en
3 citations

Abstract

Although olefin metathesis is a superior method for the construction of olefins, the synthesis of fluoroolefins remains challenging. In this study, we report the exploration of ruthenium catalysts suitable for the ring-closing metathesis of fluoroolefins. Using ruthenium catalysts with appropriate six-membered N-heterocyclic carbene ligands, we successfully synthesized various five- and six-membered fluorinated ring olefins. DFT calculations suggested that the strong electron-donating properties and moderate bulkiness of the N-heterocyclic carbene ligands played crucial roles.

Organic LettersVol. 27(6)
Tokyo Denki University (JP), Sagami Chemical Research Institute (JP)
Clean water and sanitation
Openalex Percentile: Top 12%
Synthetic Organic Chemistry Methods
2.81
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