8-Alkenylborondipyrromethene dyes. General synthesis, optical properties, and preliminary study of their reactivity

A new series of 8-alkenylBODIPY dyes were prepared via the Liebeskind–Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPY. Ten derivatives were prepared using alkenylboronic acids in good to excellent yields (79–97%), and one additional example was prepared from an alkenylstannane in...

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Bibliographic Details
Published in:Tetrahedron 2011-09, Vol.67 (38), p.7244-7250
Main Authors: Arroyo, Ismael J., Hu, Rongrong, Tang, Ben Zhong, López, Fabiola I., Peña-Cabrera, Eduardo
Format: Article
Language:English
Subjects:
Alkenylbodipy
BODIPY
Bonding
Chemical reactivity
Chemistry
Cross coupling
Derivatives
Dyes
Exact sciences and technology
Fluorescence
Heterocyclic compounds
Liebeskind–Srogl cross-coupling
Miscellaneous
Optical properties
Organic chemistry
Palladium
Preparations and properties
Reactivity and mechanisms
Synthesis (chemistry)
Tetrahedrons
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Summary:A new series of 8-alkenylBODIPY dyes were prepared via the Liebeskind–Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPY. Ten derivatives were prepared using alkenylboronic acids in good to excellent yields (79–97%), and one additional example was prepared from an alkenylstannane in 74% yield. The products display Michael acceptor-like reactivity. The alkenyl fragment quenches the fluorescence of the BODIPY core, which is turned back on by reducing the double bond. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.07.067