Silver-Mediated Fluorination of Functionalized Aryl Stannanes

Furuya, Takeru; Strom, Alexandra E.; Ritter, Tobias

doi:10.1021/ja8086664

Cited by 288 publications

(131 citation statements)

References 35 publications

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“…Preparation of demethyl quinine (cupreine) was a modified procedure adapted from procedures reported by Xu et al (36) and Furuya et al (37). A 500-ml three-necked flask equipped with an argon inlet, a reflux condenser, and a large magnetic stir bar (38 by 16 mm) was charged with N,N-dimethylformamide (DMF) (100 ml) and 95% sodium hydride (5.92 g, 247 mmol, 8 equivalents).…”

Section: Methodsmentioning

confidence: 99%

Antimalarial Efficacy of Hydroxyethylapoquinine (SN-119) and Its Derivatives

Sanders

Meyers

Sullivan

2014

Antimicrob Agents Chemother

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Section: Methodsmentioning

confidence: 99%

Antimalarial Efficacy of Hydroxyethylapoquinine (SN-119) and Its Derivatives

Sanders

Meyers

Sullivan

2014

Antimicrob Agents Chemother

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“…Naturally-occurring quinine 152, one of the simpler alkaloids, was fluorinated by Ritter's group according to two different reports. 21,22 Both reactions embody the use of an electrophilic fluorinating reagent, F-TEDA-PF6 in the presence of a silver catalyst. The overall reaction provides for the addition of a fluoride atom to the 6'-position of the aromatic ring thereby giving analogue 153 (Scheme 43).…”

Section: Alkaloids and Nitrogen Heterocyclesmentioning

confidence: 99%

Selective fluorination of natural products

Luzzio¹,

Monsen²,

Zhdankin³

2017

Arkivoc

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Compounds derived from natural sources including animals, plants, and micro-organisms have been widely used for pharmaceuticals, materials, and agrochemicals. The use of these natural products has grown increasingly over the years and the demand for more improved, biologically active, and safer derivatives of natural products has been investigated by many researchers in the areas of synthetic and medicinal chemistry. Due to the unique characteristics of fluorinated compounds, and the increased or more favorable biological activity which usually accompanies fluorinated analogues of medicinally-important compounds, the fluorination of natural products has gained much attention. This review aims at exploring the range of specific natural product types that have been selectively fluorinated as well as how fluorination was expected to affect their biological activities and physiochemical properties.

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“…In 2009, Furuya et al described the silver-catalyzed electrophilic fluorination of aryl stannanes ( Figure 6, left). 22 This catalytic transformation is applicable for late-stage fluorination of natural products and their derivatives. The proposed mechanism is distinct from conventional cross-coupling reactions and features a multinuclear high-valent aryl silver fluoride complex.…”

mentioning

confidence: 99%