Synthesis of Fluorinated Pyridines

Шестопалов, А. М.; Rodinovskaya, L. A.; Mortikov, V. Yu.; Fedorov, A. E.

doi:10.1007/978-3-319-04435-4_1

Cited by 4 publications

(4 citation statements)

References 119 publications

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“…Concerning fluorinated pyridines, 2- and 4-substituted derivatives are notably more susceptible to nucleophilic substitution of fluorine compared to 3-fluoropyridines. Correspondingly, the 3-fluoropyridine fragment is a frequently utilized unit for the design of pharmaceuticals …”

Section: Introductionmentioning

confidence: 99%

“…Existing methods toward 3-fluoropyridines rely on substitution of the diazonium group (Balz–Schiemann reaction), whereas other transformations such as electrophilic fluorination of organometallics, deoxofluorination, and nucleophilic fluorination (transition-metal-catalyzed, iodine(III) substitution, uncatalyzed halogen substitution) have been occasionally used. Several ring-forming reactions of narrow scope have also been described .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

et al. 2017

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A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy) under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

et al. 2017

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“…13 Notably, these pharmaceuticals all contain a fluorinated six-membered azaheterocycle, such as fluoro-pyridine or -pyrimidine structural sub-unit, and effective synthetic procedures at both discovery and manufacturing scales are well reported in the literature. [14][15][16][17][18][19][20][21] In contrast, it is particularly striking that pharmaceuticals bearing related five-membered azaheterocycles, such as fluorinated pyrroles, furans and thiophenes, are very rarely found in life science products and this is, in part, due to the lack of available, efficient and regioselective methodology for the synthesis of, for example, appropriate fluoropyrrole derivatives both for medicinal chemistry programmes and large scale synthesis.…”

Section: Introductionmentioning

confidence: 99%

Fluorination of pyrrole derivatives by Selectfluor™

Heeran

Sandford

2016

Tetrahedron

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“…Nitrogen heterocycles and their fluorinated analogues are ubiquitous and highly desirable motifs in pharmaceutical compounds. − While facile new syntheses of fluorinated pyridines have emerged in recent years, current methods of constructing pyridines with fluorine substitution at the 3-position either require functional group transformations upon preinstalled functionality at this site on the pyridine ring − or rely on heavily functionalized building blocks. − Herein we describe a new Rh(III)-catalyzed C–H functionalization approach to prepare 3-fluoropyridines bearing multiple substituents from α-fluoro-α,β-unsaturated oximes and alkynes.…”

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confidence: 99%

Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines

2015

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A Rh(III)-catalyzed C–H functionalization approach was developed for the preparation of multi-substituted 3-fluoropyridines from α-fluoro-α,β-unsaturated oximes and alkynes. Oximes substituted with aryl, heteroaryl and alkyl β-substituents were effective coupling partners, as were symmetrical and unsymmetrical alkynes with aryl and alkyl substituents. The first examples of coupling α,β-unsaturated oximes with terminal alkynes was also demonstrated and proceeded with uniformly high regioselectivity to provide single 3-fluoropyridine regioisomers. Reactions were also conveniently set up in air on the bench top.

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Synthesis of Fluorinated Pyridines

Cited by 4 publications

References 119 publications

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

Fluorination of pyrrole derivatives by Selectfluor™

Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines

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