Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents

Borodkin, G. I.; Zaikin, Pavel A.; Шакиров, М. М.; Shubin, V. G.

doi:10.1134/s1070428007100077

Cited by 14 publications

(10 citation statements)

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“…As part of our ongoing efforts to develop environmentally benign methods for electrophilic aromatic fluorination,, , we began to investigate the solvent‐free fluorination of electron‐rich aromatic compounds with 1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F‐TEDA‐BF 4 , Selectfluor TM , 1 ).…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes

et al. 2017

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An effective protocol for the solvent‐free fluorination of electron‐rich aromatic compounds with 1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F‐TEDA‐BF4) is described. The protocol allows the easy and efficient isolation of fluorinated products in high yields and purities with low E factors (kgwaste kgproduct–1) by vacuum‐sublimation without the use of any solvent. The solid‐state fluorination of naphthalen‐2‐ol was studied by differential thermal analysis, and scanning electron microscopy was used to obtain evidence for the solid‐state process. The crucial influence of alkali‐metal carbonates on the rate of the solvent‐free fluorination of hydroxynaphthalenes and estrone was demonstrated.

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Section: Introductionmentioning

confidence: 99%

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes

et al. 2017

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“…Among many electrophilic N-F reagents, the commercially available 1-chloromethyl-4-uoro-1,4-iazoniabicyclo[2.2.2]-octanebis-tetra-uoroborate (F-TEDA-BF 4 , Selectuor) is the most popular one (Scheme 1). 1-3 Thus, the development of mild and selective synthetic methods for incorporating uorine into organic aromatic compounds is of great importance.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor

Geng

Liu

et al. 2015

RSC Adv.

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The selective fluorination of aromatic compounds with Selectfluor has been studied theoretically. The structural and energetic features of p complexes of substituted benzenes with Selectfluor are investigated, and the fluorine bond (F/p) has been found to make an important contribution to the stabilization of the p complexes. Our calculations indicate that the SET mechanism, which involves one electron transfer from the aromatic substrate (D) to Selectfluor (A), is preferred over the S N 2 mechanism.The analysis of the minimum energy path (MEP) suggests that the DABCO moiety of Selectfluor seems to take an active role in the fluorination of aromatic compounds with Selectfluor. In addition, a two-state model analysis, as well as the characteristics of avoiding crossing between the DA and D + A À states of benzene/Selectfluor are addressed to obtain deep insight into the features of the SET mechanism.

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“…The kinetics of fluorination of mesitylene 119 with Selectfluor™ 25 were monitored using iodometric titrations by Borodkin et al in 2006. 109,110 The reactions were proposed to proceed via a σ-complex 120. Second-order rate constants were determined according to Equation 3 (Table 10).…”

Section: Kinetics Of Fluorination Of Mesitylene With Selectfluor™mentioning

confidence: 99%

Reactivities of electrophilic N–F fluorinating reagents

Rozatian

Hodgson

2021

Chem. Commun.

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Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents

Cited by 14 publications

References 39 publications

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes

Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor

Reactivities of electrophilic N–F fluorinating reagents

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Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents

Cited by 14 publications

References 39 publications

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF4: Toward “Dry” Processes

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF4: Toward “Dry” Processes

Theoretical study on the mechanism of selective fluorination of aromatic compounds with Selectfluor

Reactivities of electrophilic N–F fluorinating reagents

Contact Info

Product

Resources

About

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes

Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF₄: Toward “Dry” Processes