title: Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes.
abstract: 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.
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Palao
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Duran-Sampedro
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Santiago
authors.initials: S
authors.lastname: de la Moya
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Miriam
authors.initials: M
authors.lastname: Madrid
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Carmen
authors.initials: C
authors.lastname: García-López
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: Antonia R
authors.initials: AR
authors.lastname: Agarrabeitia
authors.affiliation: Department of Chemistry, KU Leuven , Celestijnenlaan 200 f, B-3001 Leuven, Belgium.
authors.forename: Bram
authors.initials: B
authors.lastname: Verbelen
authors.affiliation: Department of Chemistry, KU Leuven , Celestijnenlaan 200 f, B-3001 Leuven, Belgium.
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
authors.affiliation: Department of Chemistry, KU Leuven , Celestijnenlaan 200 f, B-3001 Leuven, Belgium.
authors.forename: Nöel
authors.initials: N
authors.lastname: Boens
authors.affiliation: Department of Organic Chemistry I, Universidad Complutense de Madrid, Facultad de Ciencias Químicas , Ciudad Universitaria s/n, E-28040 Madrid, Spain.
authors.forename: María J
authors.initials: MJ
authors.lastname: Ortiz