Journal of Organic Chemistry p. 3700 - 3710 (2016)
Update date:2022-08-11
Topics:
Palao, Eduardo
Duran-Sampedro, Gonzalo
De La Moya, Santiago
Madrid, Miriam
García-López, Carmen
Agarrabeitia, Antonia R.
Verbelen, Bram
Dehaen, Wim
Boens, N?el
Ortiz, María J.
The generality of the palladium-catalyzed C-C coupling Negishi reaction when applied to haloBODIPYs is demonstrated on the basis of selected starting BODIPYs, including polyhalogenated and/or asymmetrical systems, and organozinc reagents. This reaction is an interesting synthetic tool in BODIPY chemistry, mainly because it allows a valuable regioselective postfunctionalization of BODIPY chromophores with different functional groups. In this way, functional patterns that are difficult to obtain by other procedures (e.g., asymmetrically functionalized BODIPYs involving halogenated positions) can now be made. The regioselectivity is achieved by controlling the reaction conditions and is based on almost-general reactivity preferences, and the nature of the involved halogens and their positions. This ability is exemplified by the preparation of a series of new BODIPY dyes with unprecedented substitution patterns allowing noticeable lasing properties.
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