A route to fluoroalkyl-substituted aromatic compounds involving fluoroalkylcopper intermediates

McLoughlin, V. C. R.; Thrower, J. D.

doi:10.1016/s0040-4020(01)83100-8

Cited by 375 publications

(180 citation statements)

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“…4,5) The trifluoromethylation by this method has been developed by Y. Kobayashi and his co-workers not only for aromatic, but also for heterocyclic and aliphatic compounds.6) On the other hand, perfluoroalkylzinc compounds are known to be much more stable than the corresponding magnesium or lithium compounds and the preparation of heptafluoro-lmethylethylzinc iodide and its reactions with acyl halides or acid anhydrides, affording heptafluoro-l-methylethyl aryl ketones, were reported by our group.7)…”

mentioning

confidence: 95%

Trifluoromethylation of Carbonyl Compounds With Trifluoromethylzinc Iodide Under Ultrasonic Irradiation

Kitazume

Ishikawa

1981

Chemistry Letters

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mentioning

confidence: 95%

Trifluoromethylation of Carbonyl Compounds With Trifluoromethylzinc Iodide Under Ultrasonic Irradiation

Kitazume

Ishikawa

1981

Chemistry Letters

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“…Mcloughlin [13] and Kumadaki [14] reported independently, with copper powder, that CF 3 I can react with Ar-I to form Ar-CF 3 . Gradually, metal-catalyzed trifluoromethylation has been the most frequently-used method, however, several drawbacks limited their utility.…”

Section: Nucleophilic Trifluoromethylationmentioning

confidence: 99%

Research progress on trifluoromethyl-based radical reaction process

Song

2017

IOP Conf. Ser.: Earth Environ. Sci.

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Abstract. Due to the unique properties imparted by the trifluoromethyl group, such as high electron density and strong lipotropy, which effectively improve acidity, lipophilicity and metabolic stability of the molecule itself, trifluoromethyl-substituted organic compounds are becoming increasingly important as structural motifs in pharmaceuticals, agrochemicals and organic materials. In this review, we present several methods developed for the direct introduction of a trifluoromethyl group, beginning with its rich and storied history. Then the present article addresses mechanism and process in carbon-carbon bond forming reaction based on radical process which is divided into three parts according to the way of CF3 radical generation. Finally, challenges and opportunities of researches on trifluoromethylation reactions facing are prospected. IntroductionIt is well-known that organofluorine compounds are extremely rare in nature despite the relatively high abundance of fluorine in our earth's crust.The seeds of researches on fluorinated compounds were firstly planted in 1764, however, seeds didn't sprout until 1896 when Swarts successfully synthesized ethyl fluoroacetate [1]. And then the ingenious Balz-schiemann reaction moved the fluoro-organic chemistry field into a brand new stage with a better comprehension of the specific fluorine factors on the outcome of organic reactions [2].Psychotropic drugs containing F atom such as Fluphenazine was discovered in 1956 and 5-Fluorouracil in 1957 [3], brought greater hopes for cancer therapy as well as more attention on the application of fluorinated compounds. (Hetero)arenes bearing CF 3 groups constitute an indispensable part of numerous important drugs, including celecoxib, fluoxetine and fluazinam. Currently, the interest in fluoro-organic chemistry is at an all-time high.It is therefore apparent that the development of new methods for trifluoromethylation, especially in an efficient, mild and green way, is essential and necessary.It is noteworthy that new discoveries and developments of trifluoromethylation reactions are built on the researches on Trifluoromethyl reagents. Mechanisms corresponding to their regents' properties which are electrophilic, nucleophilic, or radical, can be divided into electrophilic trifluoromethylation; nucleophilic and radical. In this review, we 1) Categorize types of trifluoromethylation with presentation of the reagents in each section. 2) Introduce some recent examples of C-C bond formation based on radical way, which have appeared in the primary literature. Important earlier work in this field is also covered. 3) Focus our attention on summarizing the mechanism and propose the problems hindering the evolving chemical landscape that has engaged trifluoromethylation reactions.

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“…8 The reaction vessel was heated at l 05°C for 24 h. After cooling the mixture, it was poured into ether and the precipitate was removed by filtration. The filtrate was washed with dil HCl and then with aq NaHSO 3 , dried over anhydrous MgSO 4 , and distilled to give la (9.58 g, 57% yield).…”

Section: Preparation Of Monomers L-perfluoroalkyl-4-trifluorome Thy/bmentioning

confidence: 99%

Preparation and Properties of Poly(phenylacetylene) Membranes Containing Perfluoroalkyl Groups

Hayakawa

Nishida

Fukaya

et al. 1993

Polym J

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A route to fluoroalkyl-substituted aromatic compounds involving fluoroalkylcopper intermediates

Cited by 375 publications

References 20 publications

Trifluoromethylation of Carbonyl Compounds With Trifluoromethylzinc Iodide Under Ultrasonic Irradiation

Trifluoromethylation of Carbonyl Compounds With Trifluoromethylzinc Iodide Under Ultrasonic Irradiation

Research progress on trifluoromethyl-based radical reaction process

Preparation and Properties of Poly(phenylacetylene) Membranes Containing Perfluoroalkyl Groups

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