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Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives

Author:
Savoldelli, Andrea, Meng, Qianli, Paolesse, Roberto, Fronczek, Frank R., Smith, Kevin M., Vicente, M. Graça H.
Source:
Journal of organic chemistry 2018 v.83 no.12 pp. 6498-6507
ISSN:
1520-6904
Subject:
Lewis bases, chemical structure, cross-coupling reactions, medicine, organic chemistry, organic compounds, regioselectivity
Abstract:
A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials.
Agid:
6047305