electrophilic fluorination
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2021 ◽  
Author(s):  
Masayuki Komatsuda ◽  
Ayane Suto ◽  
Hiroki Kondo Jr. ◽  
Hiroyuki Takada ◽  
Kenta Kato ◽  
...  

We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.


2021 ◽  
Author(s):  
Masayuki Komatsuda ◽  
Ayane Suto ◽  
Hiroki Kondo Jr. ◽  
Hiroyuki Takada ◽  
Kenta Kato ◽  
...  

We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.


Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5756
Author(s):  
Pavel A. Zaikin ◽  
Ok Ton Dyan ◽  
Innokenty R. Elanov ◽  
Gennady I. Borodkin

We demonstrated the influence of liquid additives on the rate and selectivity of mechanochemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichiometric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.


Author(s):  
Gaurav Bahuguna ◽  
Mohit Verma ◽  
Ritu Gupta

Recently, there has been substantial interest in the fluorination of nanomaterial thin films used in various optoelectronic devices for optimum charge transport across semiconducting layers. The discovery of electrophilic fluorinating...


Author(s):  
Chun-Xiang Guo ◽  
Sivathmeehan Yogendra ◽  
Rosa M. Gomila ◽  
Antonio Frontera ◽  
Felix Hennersdorf ◽  
...  

The in situ one-pot electrophilic fluorination of phosphanes with NFSI followed by anion exchange with MeOTf gives highly electrophilic fluorophosphonium triflates – highly efficient catalysts for the synthesis of N-sulfonylamidines from amides.


2020 ◽  
Vol 240 ◽  
pp. 109670
Author(s):  
Wang Li ◽  
Tsugio Kitamura ◽  
Yangliu Zhou ◽  
Greg Butler ◽  
Jianlin Han ◽  
...  

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