Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

Recsei, Carl; Barda, Yaniv

doi:10.3762/bjoc.17.70

Cited by 3 publications

(3 citation statements)

References 12 publications

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“…[51] In 2021, Recsei and Barda developed an interesting methodology to access bis(aryloxy)fluoromethanes. [52] The proposed mechanism involved bromofluoro carbene generation from dibromofluoromethane (Br 2 FCH), K 3 PO 4 , or KOH. In this reaction, aryloxide I5 undergoes addition to carbene I6, followed by bromide elimination to form the second carbene I9, which is further trapped by another molecule of aryloxide I5.…”

Section: Fluorohalocarbenesmentioning

confidence: 99%

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Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

Sperga,

Veliks

2023

Chemistry A European J

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The synthesis of monofluorinated compounds is of great interest because of the vast applications of organofluorine compounds. Recently, the introduction of monofluorocarbene synthons has emerged as an important strategy for the synthesis of fluorine‐containing products. In contrast to direct fluorination, in which C−F bonds are formed, the use of monofluorinated carbenes and related reactive species involves C−C or C−X bond formation while delivering valuable fluorine atoms into the target structure. Owing to increased knowledge on carbon‐carbon and carbon‐heteroatom bond formations, monofluorinated carbenes have enormous potential for the synthesis of organofluorine compounds, which, in our opinion, has not yet been fully exploited. This review summarizes the recent advances in the synthetic applications of monofluorinated carbenes, carbenoids, ylides, and related species.

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Section: Fluorohalocarbenesmentioning

confidence: 99%

“…In 2021, Recsei and Barda developed an interesting methodology to access bis(aryloxy)fluoromethanes [52] . The proposed mechanism involved bromofluoro carbene generation from dibromofluoromethane (Br 2 FCH), K 3 PO 4 , or KOH.…”

Section: Fluorohalocarbenesmentioning

confidence: 99%

Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

Sperga,

Veliks

2023

Chemistry A European J

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“…In contrast to difluorocarbene transfer, − fluorohalocarbene transfer reagents and reactions are far less developed (Figure ). − …”

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confidence: 99%

Fluorohalomethylsulfonium Salts as a Fluorohalocarbene Source

Sperga,

Pfeifers,

Zacs

et al. 2024

Org. Lett.

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Synthesis of fluoroorganic compounds is of great importance due to their extensive application in medicinal chemistry, agrochemicals, and materials. Herein, we report efficient synthesis of novel diaryl fluorohalomethyl sulfonium salts. The application showcased proficient reagents for Freon-free fluorochloro-, fluorobromo-, and fluoroiodocarbene transfer to alkenes. The developed mild, room temperature conditions for the cyclopropanation do not require any metal catalysts and allow synthetic access to diverse cyclopropanes.

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Accessing structurally diverse aryl difluoromethyl ethers with bromo(difluoro)acetic acid

Kumawat,

Natte

2024

Chem. Commun.

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Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

Abstract: A side-product present in the herbicide pyroxasulfone was synthesized. The construction of a bis(aryloxy)fluoromethane moiety was necessary, for which no existing method was available. We report a simple, new procedure which we applied to the synthesis of some of these unusual structures.

Cited by 3 publications

References 12 publications

Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

Fluorohalomethylsulfonium Salts as a Fluorohalocarbene Source

Accessing structurally diverse aryl difluoromethyl ethers with bromo(difluoro)acetic acid

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