Title: Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy
Authors: Boens, Noël
Verbelen, Bram
Dehaen, Wim
Issue Date: 18-Aug-2015
Publisher: Wiley-VCH
Series Title: European Journal of Organic Chemistry vol:2015 issue:30 pages:6577-6595
Abstract: In this review we describe the various new methodologies for synthetic postmodification of the BODIPY core designed and developed by our research groups, as well as their electronic spectroscopic properties. We discuss the different strategies created for functionalization of the BODIPY framework at the pyrrole C-ring positions and the meso-position. Halogenated boron dipyrrins are substrates for nucleophilic substitution or Pd-catalyzed cross-coupling reactions. α-Unsubstituted BODIPYs can be functionalized with N and C nucleophiles through oxidative or vicarious nucleophilic substitution (VNS) of the α-hydrogen atoms. Combining this methodology with reversible Michael addition onto nitrostyrenes provides a route to 3-styrylated BODIPYs. Furthermore, the one-step, Pd-catalyzed C–H arylation of 3,5-unsubstituted BODIPYs leads to 3- and 3,5-arylated dyes. Finally, radical C–H arylation at the 3,5-positions of α-unsubstituted BODIPYs provides an additional synthesis route to arylated dyes.
ISSN: 1434-193X
Publication status: published
KU Leuven publication type: RE
Appears in Collections:Molecular Design and Synthesis

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