Trifluoromethoxypyrazines: Preparation and Properties

The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a "pseudohalogen" character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, a...

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Published inMolecules (Basel, Switzerland) Vol. 25; no. 9; p. 2226
Main Authors Sokolenko, Taras M, Yagupolskii, Yurii L
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 09.05.2020
MDPI
Subjects
Amination
antimony trifluoride
Catalysis
Chemical properties
Chemical reactions
chlorination
Chlorine
coupling reactions
fluorination
Fluorine
Halogenation
Molecular Structure
Organic chemistry
Potassium
Proton Magnetic Resonance Spectroscopy
pyrazine
Pyrazines - chemical synthesis
Pyrazines - chemistry
trifluoromethoxy group
Palo Alto California
United States > US
pyrazine
fluorination
chlorination
antimony trifluoride
coupling reactions
trifluoromethoxy group
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Summary:The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a "pseudohalogen" character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less studied. As trifluoromethoxy-substituted pyrazines are still unknown, we have developed efficient and scalable methods for 2-chloro-5-trifluoromethoxypyrazine synthesis, showing the synthetic utility of this molecule for Buchwald-Hartwig amination and the Kumada-Corriu and Suzuki and Sonogashira coupling reactions. Some comparisons of chlorine atom and trifluoromethoxy group stability in these transformations have been carried out.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25092226