Asymmetric meso-CF3-dipyrromethanes with amino- and heterocyclic functions from trifluoro(pyrrolyl)ethanols and pyrroles

[Display omitted] •AlCl3 is the new effective catalyst for the synthesis of asymmetric meso-CF3-dipyrromethanes.•Approach to new dipyrromethanes – precursors of BODIPY dyes and metal complexes – was described.•Excess of catalyst could cause disproportionation. Asymmetric meso-CF3-dipyrromethanes wit...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2020-03, Vol.231, p.1-6, Article 109455
Main Authors: Tomilin, Denis N., Sobenina, Lyubov N., Petrova, Olga V., Sagitova, Elena F., Budaev, Arsalan B., Ushakov, Igor A., Ivanov, Andrey V., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
Aluminum chloride
Asymmetry
Catalysts
Condensation
Meso-CF3-dipyrromethanes
Phosphorus pentoxide
Pyrazole
Pyrroles
Trifluoro(pyrrolyl)ethanols
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Summary:[Display omitted] •AlCl3 is the new effective catalyst for the synthesis of asymmetric meso-CF3-dipyrromethanes.•Approach to new dipyrromethanes – precursors of BODIPY dyes and metal complexes – was described.•Excess of catalyst could cause disproportionation. Asymmetric meso-CF3-dipyrromethanes with amino- and nitrogen heterocyclic functions, a new family of the BODIPY dye precursors, have been synthesized in 70–90 % yield by condensation of trifluoro(pyrrolyl)ethanols with pyrroles in the presence of AlCl3. This catalyst, for the first time, was shown to be more efficient than commonly used P2O5, which was entirely inactive in the condensation of pyrroles having basic substituents (amino group and pyrazole moiety).
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2020.109455