Synthesis of fluorinated triazole and isoxazole derivatives by electrochemical fluorination

Kuribayashi, Shunsuke; Shida, Naoki; Inagi, Shinsuke

doi:10.1016/j.tet.2016.07.016

Cited by 25 publications

(9 citation statements)

References 18 publications

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“…Recent approaches focused on the use of ionic liquids as solvents, and aromatic compounds as substrates − were found to be promising for further scale up of fluorination electrosynthesis.…”

Section: Industrial Electrosynthesismentioning

confidence: 99%

Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications

Cardoso

Šljukić

Santos

et al. 2017

Org. Process Res. Dev.

206

144

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Organic electrosynthesis has received great attention as a powerful green tool for synthesis, affording less waste production, less chemicals spent, and often fewer reaction steps than conventional methods. Functional group interconversion and C−C bond generation by imposition of a proper electrode potential is what lies behind organic electrosynthesis processes. Paired electrochemical reactions, indirect electrosynthesis, electrochemical microreactors, and the use of ionic liquids are some of the highlighted means that contribute to optimization of the overall process. Necessity to use specific organic solvents combined with supporting electrolytes is one of the main limitations to be overcome to make the electrochemical process more economically feasible when compared to nonelectrochemical processes. Numerous examples from the bench scale to industrial routes such as adiponitrile, substituted benzaldehydes, anthraquinone, fluorinated products, and succinic acid production are well described throughout this review.

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Section: Industrial Electrosynthesismentioning

confidence: 99%

Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications

Cardoso

Šljukić

Santos

et al. 2017

Org. Process Res. Dev.

206

144

View full text Add to dashboard Cite

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“…Synthesis of various dipolarophiles (acetylene) ( 4a‐h ) was carried out as per the procedure reported in the literature. [ 35–38 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis of chalcone precursor via Cu(I) catalyzed 1,3‐dipolar reaction of functionalized acetylene and pyrazole embedded dipole

Manju

Kalluraya

Asma

et al. 2020

Journal of Heterocyclic Chem

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A new class of functionalized pyrazole bearing 1,2,3-triazole has been synthesized via Cu(I) mediated 1,3-dipolar cycloaddition of pyrazole bearing azide with various aromatic/heteroaromatic bearing terminal dipolarophile (acetylene). Structures of the newly synthesized compounds were explicated by analytical and spectral analysis. All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antioxidant activity. Among the synthesized compound, triazole bearing 2,5-thiazolidinone 5b (20 ± 0.70) and triazole bearing thiocarboamide 5e (19 ± 0.70) showed good antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, respectively. The newly synthesized compounds further tested for their ability to bleach DPPH radical using DPPH scavenging assay. Among the synthesized compounds 1,2,3-triazole bearing 2,5-thiazolidinone 5b (58.81%) exhibited good DPPH scavenging activity compared to the rest of the compounds. From the X-ray and Hirshfield analysis, it was observed that compound 3, crystallizes in a triclinic crystal system with a P-1 space group. The major intercontacts present in these molecules are H…H (39.7%), C…H (23.9%), N…H (20.3%).

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“…Analogous as described in [ 17 ], the anodic oxidation of a substrate (1 mmol) was carried out in a plastic undivided cell equipped with platinum anode and cathode (2 cm × 2 cm) containing 10 mL of HF salt (20 equiv of F − to substrate/solvent) at room temperature. A constant current (40 mA) was passed until the starting material was mostly consumed (monitored by TLC).…”

Section: Methodsmentioning

confidence: 99%

The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives

Kuribayashi¹,

Kurioka²,

Inagi³

et al. 2018

Beilstein J. Org. Chem.

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We herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing Et4NF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.

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Synthesis of fluorinated triazole and isoxazole derivatives by electrochemical fluorination

Cited by 25 publications

References 18 publications

Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications

Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications

Synthesis of chalcone precursor via Cu(I) catalyzed 1,3‐dipolar reaction of functionalized acetylene and pyrazole embedded dipole

The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives

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