Fluorination Reactions of Sulfur Tetrafluoride

Smith, W. C.; Tullock, C. W.; Muetterties, E. L.; Hasek, William R.; Fawcett, Frank S.; Engelhardt, V. A.; Coffman, D. D.

doi:10.1021/ja01521a086

Cited by 54 publications

(36 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1a). Since the first report on the SF 4 -mediated deoxyfluorination reactions13, dozens of power-variable deoxyfluorination reagents have been developed89101112. Generally, these reagents can be divided into two categories: one is the sulfur fluorides and their derivatives (SF reagents)1415161718 (Fig.…”

mentioning

confidence: 99%

Deoxyfluorination of alcohols with 3,3-difluoro-1,2-diarylcyclopropenes

Wang

et al. 2016

Nat Commun

View full text Add to dashboard Cite

Aromatic cation activation is a useful strategy to promote deoxyfunctionalization; however, the deoxyfluorination of alcohols with cyclopropenium cation remains an unsolved problem due to the weak nucleophilicity of fluoride ion. Here we report the use of 3,3-difluoro-1,2-diarylcyclopropenes (CpFluors) as easily accessible and reactivity-tunable deoxyfluorination reagents. The electronic nature of CpFluors is critical for fluorination of monoalcohols via alkoxycyclopropenium cations, and CpFluors with electron-rich aryl substituents facilitate the transformation with high efficiency; however, selective monofluorination of 1,2- and 1,3-diols, which proceeds via cyclopropenone acetals, is less dependent on the electronic nature of CpFluors. Moreover, CpFluors are more sensitive to the electronic nature of alcohols than many other deoxyfluorination reagents, thus fluorination of longer diols can be achieved selectively at the relatively electron-rich position. This research not only unveils the first example of deoxyfluorination reagents that contain an all-carbon scaffold, but also sheds light on the divergent reactivity of cyclopropenium cation in deoxyfunctionalization of alcohols.

show abstract

mentioning

confidence: 99%

Deoxyfluorination of alcohols with 3,3-difluoro-1,2-diarylcyclopropenes

Wang

et al. 2016

Nat Commun

View full text Add to dashboard Cite

show abstract

“…One of the efficient methods was using sulfur tetrafluoride, which was first introduced by Engelhardt group [59,60]. An acid (starting material) was placed in 500 mL autoclave, it was cooled by liquid nitrogen and anhydrous hydrofluoric acid (HF) was added.…”

Section: Deoxyfluorination Of Aromatic Acidsmentioning

confidence: 99%

Recent Development of Trifluoromethyl Reagents: A Review

Bhowmick

2021

J. Sci. Res.

View full text Add to dashboard Cite

Organic molecules having fluorine atom are very important since it increases the lipophilicity that is essential for drug development and additionally strong carbon-fluorine (C-F) bond makes the material unique, especially for material chemistry. Instead of elemental fluorine, recently trifluoromethylated materials (CF3) have drawn considerable attention in the agrochemical and pharmaceutical industries. In the continuous development of the trifluoromethylated reagents, over the last few decades, some trifluoromethylated reagents have been well developed and the efficiency of these reagents for incorporating CF3 group on different types of substrates are also studied. In this article, all types of available trifluoromethylated reagents and their effectiveness on suitable substrates are summarized. Additionally, the methods of synthesizing trifluoromethylated substrates are discussed. Finally, the scopes of the development of new reagents after focusing on the shortcomings of the current reagents are also discussed.

show abstract

“…Ionic liquids can promote nucleophilic substitutions with fluoride and diminish the formation of byproducts. 9 6.06.1.1.2 Deoxyfluorination and dethiofluorination approaches Toxic and volatile sulfur tetrafluoride, reported to convert carbonyl groups to germinal difluoromethylene groups, 15 is undesirable to use and lead to the development of less volatile reagents such as aryl and aminosulfur trifluorides. Diethylaminosulfur trifluoride (DAST) 11i, 16 is a moisture-sensitive, explosive (when heated) reagent 11e that is most commonly used for deoxyfluorination of carbonyl and hydroxyl groups or fluorodesulfurization of thiocarbonyl or sulfide groups.…”

Section: Synthesis Of Alkyl Fluoridesmentioning

confidence: 99%