Trifluoromethylations and related reactions in organic chemistry

Mcclinton, M. A.; McClinton, Deborah A.

doi:10.1016/s0040-4020(01)80011-9

Cited by 593 publications

(240 citation statements)

References 241 publications

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“…[66,67] It should be noted that the reduction of acetylenic CF 3 ketones using LiAlH 4 or NaBH 4 does not give CF 3 enones but the corresponding allyl alcohols [50,64,68]. The diastereoselective reduction of CF 3 enones with baker's yeast was also investigated (Scheme 23).…”

Section: Scheme 21mentioning

confidence: 99%

“…There are two general approaches: 1) fluorination of an existing heterocyclic ring including functional group transformations [4], for example transformation of a carboxy moiety to a trifluoromethyl group [5] or the trifluoromethylation of heterocycles using CF 3 Cu [6,7] or CF 3 radicals [8,9]. 2) construction of heterocyclic rings using fluorinated synthons.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Preparation of α,β-Unsaturated Ketones Bearing a Trifluoromethyl Group and Their Application in Organic Synthesis

1997

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Section: Scheme 21mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of α,β-Unsaturated Ketones Bearing a Trifluoromethyl Group and Their Application in Organic Synthesis

1997

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“…The key to these nucleophilic regents preparation is to the formation of CF 3 -with metal catalyzed. In the early stage, trifluoromethyl metal species (Hg, Cu, Zn, and Cd) have been extensively investigated [12].…”

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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“…A non-comprehensive list of recent reviews is given in references 3-19. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Some of the challenges for the preparation of organofluorine derivatives lay on the development of suitable fluorine reagents that are not too reactive, as fluorine itself, or too unreactive because in order to give the desired reaction there is the need of the cleavage of a strong E-F bond. Some of the well developed and useful catalytic reactions for non-fluorinated compounds have been applied to the synthesis of fluoroderivatives but, in many cases, the reactions are not as effective as expected or simply do not work.…”

Section: Introductionmentioning

confidence: 99%