Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)

Hirotaki, Kensuke; Kawazoe, Genyu; Hanamoto, Takeshi

doi:10.1016/j.jfluchem.2014.07.018

Cited by 13 publications

(11 citation statements)

References 33 publications

(31 reference statements)

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“…It was found, that under usual conditions of the reaction (equal amount of N 2 H 4 ·H 2 O, DMSO or EtOH as a solvent) the yields of the desired alkenes were not good enough. Better results were obtained in ethylene glycol with a 4-fold excess of N 2 H 4 ·H 2 O (novel media just reported for COR [ 37 ]). In this case, target alkenes were isolated in up to 62% yield.…”

Section: Resultsmentioning

confidence: 98%

“…Acetylferrocene and 1,1’-diacetylferrocene were also involved successfully into this transformation ( Scheme 4 ). Our preliminary study of the catalytic olefination of acetylferrocene by CF 3 CBr 3 (alkene 8 ) and CBr 4 (alkene 7 ) indicates, that in contrast to ferrocene carbaldehyde, better results were achieved in DMSO using previously prepared hydrazones [ 37 ]. A series of ferrocene derivatives including fluorinated ones was prepared in good yields.…”

Section: Resultsmentioning

confidence: 99%

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A new approach to ferrocene derived alkenes via copper-catalyzed olefination

Muzalevskiy¹,

Shastin²,

Demidovich³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA new approach to ferrocenyl haloalkenes and bis-alkenes was elaborated. The key procedure involves copper catalyzed olefination of N-unsubstituted hydrazones, obtained from ferrocene-containing carbonyl compounds and hydrazine, with polyhaloalkanes. The procedure is simple, cheap and could be applied for the utilization of environmentally harmful polyhalocarbons. The cyclic voltammetry study of the representative examples of the synthesized ferrocenyl alkenes shows the strong dependence of the cathodic behavior on the amount of vinyl groups: while for the monoalkene containing molecules no reduction is seen, the divinyl products are reduced in several steps.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

Muzalevskiy¹,

Shastin²,

Demidovich³

et al. 2015

Beilstein J. Org. Chem.

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“…First, we investigated olefination of 2-nitrobenzaldehydes 1 to prepare the corresponding trifluoromethylated styrenes 2 . The catalytic olefination reaction (COR) [ 15 , 86 , 87 , 88 , 89 , 90 ] and Wittig reaction were used for the synthesis of these alkenes. We performed screening of the reaction conditions for COR (see Supplementary Materials, Scheme S1 ).…”

Section: Resultsmentioning

confidence: 99%

“…We performed screening of the reaction conditions for COR (see Supplementary Materials, Scheme S1 ). It was found, that ethylene glycol [ 89 ] is the solvent of choice for these substrates, in contrast to EtOH traditionally used for COR with CF 3 CCl 3 [ 90 ]. It was also found, that the yield is very sensitive to the nature of the substituents (additional to ortho -nitro group) in aryl ring.…”

Section: Resultsmentioning

confidence: 99%

An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes

et al. 2021

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The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3CCl3 afforded stereoselectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF3-indole.

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“…All reagents, ketones, aldehydes, and solvents were purchased from commercial suppliers and used without purification unless stated otherwise. Hydrazones 2 , 15 13 , 16 14 , 17 15 , 18 and 27 (19) were prepared using literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles

et al. 2018

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The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I 2 /cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellent yields. Reaction of hydrazones of aldehydes with 2′-aryloxy ketones in the presence of cat. HCl in ethanol and the catalyst-free reaction of phenacyl bromides with hydrazones of aldehydes in ethanol also gave good to excellent yields of 3,5-diarylpyrazoles.

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Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)

Cited by 13 publications

References 33 publications

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes

Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles

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