Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes
| Autor: | Noël Boens, Antonia R. Agarrabeitia, Miriam Madrid, Wim Dehaen, Santiago de la Moya, Maria J. Ortiz, Eduardo Palao, Gonzalo Duran-Sampedro, Carmen García-López, Bram Verbelen |
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| Rok vydání: | 2016 |
| Předmět: |
Reaction conditions
Dye laser 010405 organic chemistry Negishi coupling Organic Chemistry Regioselectivity Chromophore 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Organic chemistry Reactivity (chemistry) BODIPY |
| Zdroj: | The Journal of Organic Chemistry. 81:3700-3710 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 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. ispartof: Journal of Organic Chemistry vol:81 issue:9 pages:3700-3710 ispartof: location:United States status: published |
| Databáze: | OpenAIRE |
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