Regioselective and Stepwise Syntheses of Functionalized BODIPY Dyes through Palladium-Catalyzed Cross-Coupling Reactions and Direct C-H Arylations

摘要

Regioselective and stepwise syntheses of a series of functionalized BODIPY dyes through palladium catalyzed cross-coupling reactions and direct C-H arylations have been developed. In particular, this method allows the straightforward synthesis of 2,6-dibromo-3,5-diary1BODIPYs and 2-bromo-3-ary1BODIPYs from polybrominated BODIPYs. The X-ray structure of intermediates 5a-c indicated that the palladium was first inserted into the C-Br bonds at 3,5 positions of brominated BODIPYs. The resulting 2,6-dibromosubstituted BODIPYs are potential long wavelength photo sensitizers which are not easily accessible using previous methods.