Silver-mediated fluorination of aryl silanes

Tang, Pingping; Ritter, Tobias

doi:10.1016/j.tet.2011.02.077

Cited by 102 publications

(95 citation statements)

References 60 publications

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“…If dimethyl ether was used (with even greater solubilizing power) the rate of reaction appeared to increase (more rapid color changes), but not the isolated yield. Future efforts towards fluorinated metallocenes might benefit from recent developments in transition metal-catalyzed fluorinations (for example, from phenols, 22 aryl triflates, 23 stannanes, 24 boronic acids, 25 silanes 26 or iodides 27 ). 28 As with FcCl and fcCl 2 , aqueous FeCl 3 was used to remove FcH and FcH/FcF impurities from FcF and fcF 2 , respectively (Table 1).…”

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confidence: 99%

The Unusual Redox Properties of Fluoroferrocenes Revealed through a Comprehensive Study of the Haloferrocenes

Inkpen

Hildebrand

et al. 2015

Organometallics

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ABSTRACT:We report the synthesis and full characterization of the entire haloferrocene (FcX) and 1,1'-dihaloferrocene (fcX 2 ) series (X = I, Br, Cl, F; Fc = ferrocenyl, fc = ferrocene-1,1'-diyl). Finalization of this simple, yet intriguing set of compounds has been delayed by synthetic challenges associated with the incorporation of fluorine substituents. Successful preparation of fluoroferrocene (FcF) and 1,1'-difluoroferrocene (fcF 2 ) were ultimately achieved using reactions between the appropriate lithiated ferrocene species and N-fluorobenzenesulfonimide (NFSI). The crude reaction products, in addition to those resulting from analogous preparations of chloroferrocene (FcCl) and 1,1'-dichloroferrocene (fcCl 2 ), were utilized as model systems to probe the limits of a previously reported 'oxidative purification' methodology. From this investigation and careful solution voltammetry studies, we find that the fluorinated derivatives exhibit the lowest redox potentials of each of the FcX and fcX 2 series. This counter-intuitive result is discussed with reference to the spectroscopic, structural and first principles calculations of these and related materials.

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confidence: 99%

The Unusual Redox Properties of Fluoroferrocenes Revealed through a Comprehensive Study of the Haloferrocenes

Inkpen

Hildebrand

et al. 2015

Organometallics

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“…More recently, silver-mediated fluorination of arylboronic acids [102,158], aryl silanes [103,159], and aryl stannanes [104,160] has been reported using Selectfluor (Fig. 63).…”

Section: Fig 58mentioning

confidence: 99%

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Campbell

Hoover

Ritter

2014

Topics in Organometallic Chemistry

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The development of new C-F bond forming reactions from organotransition metal complexes has played a key role in advancing the field of fluorination chemistry and has allowed for improved access to fluorinated organic molecules of interest in medicine, materials, and agrochemicals. In this review, we describe the development of transition metal-mediated and metal-catalyzed fluorination methods over the past decade. Special attention is paid to the variety of organometallic mechanisms by which C-F bond formation can occur and the strengths and limitations of different approaches.

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“…174 Silver salts were used to mediate the fluorination of arylstannanes, 175 boronic acids, 176 and silanes. 177 Presence of a putative multimetallic, high-valent silver species is postulated to be the facilitating factor for aryl fluoride reductive elimination at room temperature. This silver salt-based fluorination method can accomplish the fluorination of nitrogenous heteroaryl and mesityl nucleophiles as well as nucleophiles containing electron-rich, electron-poor, electrophilic, and protic functional groups.…”

Section: Transition Metal-mediated Fluorinationmentioning

confidence: 99%