Synthesis of trifluoromethyl fluoroformate from trifluoromethyl hypofluorite and carbon monoxide: Thermal and catalyzed reaction

Du, Libin; DesMarteau, Darryl D.; Tortelli, V.; Galimberti, Maurizio

doi:10.1016/j.jfluchem.2009.07.004

Cited by 11 publications

(6 citation statements)

References 27 publications

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“…Later, they improved the synthetic route by initiating the reaction of CF 3 OF/CO with the sterically hindered halogenated olefins ( 212 ) or by heating the reaction at high temperatures in a proper tubular reactor (Scheme 37). [67b] Compared to the previous method, these procedures avoided the use of fluorine gas and gave yields of up to 80 %. The thermal reaction of CF 3 OF and CO in a flow system was highly dependent upon the temperature and the type of tubular reactor material.…”

Section: Synthesis and Transformation Of Fluoroformates And Their Ana...mentioning

confidence: 97%

Recent Advances in the Synthesis and Transformation of Carbamoyl Fluorides, Fluoroformates, and Their Analogues

Liu

Zhang

2023

The Chemical Record

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Carbamoyl fluorides, fluoroformates, and their analogues are a class of important compounds and have been evidenced as versatile building blocks for the preparation of useful molecules in organic chemistry. While major achievements were made in the synthesis of carbamoyl fluorides, fluoroformates, and their analogues in the last half of 20th century, an increasing number of reports have focused on using O/S/Se=CF2 species or their equivalents as the fluorocarbonylation reagents for the direct construction of these compounds from the parent heteroatom‐nucleophiles in recent years. This review mainly summarizes the advances in the synthesis and typical application of carbamoyl fluorides, fluoroformates, and their analogues by the halide exchanges and fluorocarbonylation reactions since 1980.

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Section: Synthesis and Transformation Of Fluoroformates And Their Ana...mentioning

confidence: 97%

Recent Advances in the Synthesis and Transformation of Carbamoyl Fluorides, Fluoroformates, and Their Analogues

Liu

Zhang

2023

The Chemical Record

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“…Tang and colleagues [88] have accomplished the electron‐transfer trifluoromethoxylation of benzylic C−H bonds employing TFMS as trifluoromethoxylating reagent. This work has been reviewed before by Tang [21] and Ngai [19] .…”

Section: Trifluoromethoxylation Of Csp3 Centersmentioning

confidence: 99%

“…The authors [88] attempted to synthesize bis (trifluoromethoxylated) benzyl derivatives with an excess of TFMS reagent. Surprisingly, α‐fluorobenzyl trifluoromethyl ethers were obtained when 1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis (trifluoromethanesulfonate) (F‐TEDA‐OTf) was used as oxidant [89] .…”

Section: Trifluoromethoxylation Of Csp3 Centersmentioning

confidence: 99%

Trifluoromethoxylation Reactions of (Hetero) arenes, Olefinic Systems and Aliphatic Saturated Substrates

Barata‐Vallejo

Bonesi

Postigo³

2022

Chemistry A European J

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Directfluoroalkoxylation reactions of (hetero)arenes, carbon-carbon multiple bonds, and substitution reactions at Csp 3 carbon centers by CF 3 O, CHF 2 O, and (CF 3 ) 2 CFO groups are discussed. Emphasis on thermal radical, electron transfer, photocatalytic, electrochemical and redox-neutral radical methods are placed to accomplish fluoroalkoxylation reactions. All these methods employ either radical fluoroalkoxylating reagents or some nucleophilic trifluoromethoxylating sources of CF 3 O. A summary of all these methods is provided in Table 2.

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“…[12] Currently,there are no reports of this transformation using C À Hfunctionalization. Methods for the introduction of afluorine atom and at rifluoromethoxy group at the same site are particularly rare.…”

mentioning

confidence: 99%

“…Methods for the introduction of afluorine atom and at rifluoromethoxy group at the same site are particularly rare. [12] Currently,there are no reports of this transformation using C À Hfunctionalization. Thus,wewere very interested in investigating this reaction.…”

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confidence: 99%

Silver‐Promoted Oxidative Benzylic C−H Trifluoromethoxylation

et al. 2018

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Asilver-promoted oxidative benzylic C À Htrifluoromethoxylation has been reported for the first time.W ith trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent, various arenes,h aving diverse functional groups, undergo trifluoromethoxylation of their benzylic C À Hb onds to form trifluoromethyl ethers under mild reaction conditions. In addition, the trifluoromethoxylation and the fluorination of methyl groups of electron-rich arenes have been achieved to prepare a-fluorobenzyl trifluoromethyl ethers in one step.

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Synthesis of trifluoromethyl fluoroformate from trifluoromethyl hypofluorite and carbon monoxide: Thermal and catalyzed reaction

Cited by 11 publications

References 27 publications

Recent Advances in the Synthesis and Transformation of Carbamoyl Fluorides, Fluoroformates, and Their Analogues

Recent Advances in the Synthesis and Transformation of Carbamoyl Fluorides, Fluoroformates, and Their Analogues

Trifluoromethoxylation Reactions of (Hetero) arenes, Olefinic Systems and Aliphatic Saturated Substrates

Silver‐Promoted Oxidative Benzylic C−H Trifluoromethoxylation

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