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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Azoles as reactive nucleophiles with cyclic perfluoroalkenes
Sonali Garg1, Brendan Twamley, Zhuo Zeng
1Department of Chemistry, University of Idaho, Moscow, D 83844-2343, USA.
New fluorocyclic compounds were synthesized using azoles like imidazole and triazole. These reactions allow for multiple azole substitutions on fluorinated rings, controlled by stoichiometry.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
- Heterocyclic Chemistry
Background:
- Perfluorocycloalkenes are versatile building blocks in organic synthesis.
- Azoles, such as imidazole and triazole, are important heterocyclic compounds with diverse applications.
- Nucleophilic substitution reactions are key transformations in organic chemistry.
Purpose of the Study:
- To synthesize novel di- and multiazole-substituted fluorocyclic products.
- To investigate the reactivity of azoles with perfluorocycloalkenes.
- To explore the influence of stoichiometry on the degree of azole substitution.
Main Methods:
- Nucleophilic substitution reactions between perfluorocycloalkenes and azoles (imidazole, triazole).
- Investigation of reactions with N-substituted 1-(trimethylsilyl)-imidazole and 1-(trimethylsilyl)-1,2,4-triazole.
- Characterization of new compounds using elemental analysis, NMR spectroscopy (19F, 1H, 13C), and differential scanning calorimetry (DSC).
Main Results:
- Readily synthesized di- and multiazole-substituted fluorocyclic products (2-13) in good to high yields.
- Demonstrated reactivity of azoles with both vinylic and allylic fluorine atoms.
- Achieved substitution of up to six azoles on the fluorinated rings, with stoichiometry being a critical factor.
Conclusions:
- Developed a straightforward method for synthesizing highly azole-substituted fluorocyclic compounds.
- Highlighted the versatility of azoles in reacting with perfluorocycloalkenes.
- Established stoichiometry as a key parameter for controlling the extent of substitution in these reactions.
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