Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO

Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluores...

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Bibliographic Details
Published in:Tetrahedron letters 2014-03, Vol.55 (11), p.1946-1948
Main Authors: Mase, Nobuyuki, Ando, Taishi, Shibagaki, Fumiya, Sugita, Atsushi, Narumi, Tetsuo, Toda, Mitsuo, Watanabe, Naoharu, Tanaka, Fujie
Format: Article
Language:English
Subjects:
Aldehydes
Bearing
Carbon[sbnd]carbon bond formation
Catalysis
Fluorescence
Fluorescent molecules
Fluorogenic probe
Formations
High-throughput screening
Monitoring
Organocatalysis
Sensors
Tetrahedrons
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Summary:Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.02.007