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Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes

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Palao Utiel, Eduardo and Durán Sampedro, Gonzalo and Moya Cerero, Santiago de la and Madrid, Miriam and García López, Carmen and Rodríguez Agarrabeitia, Antonia and Verbelen, Bram and Dehaen, Wim and Boens, Nöel and Ortíz García, María Josefa (2016) Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes. Journal of organic chemistry, 81 (9). pp. 3700-3710. ISSN 0022-3263 (Print) 1520-6904(Online)

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Official URL: https://doi.org/10.1021/acs.joc.6b00350




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.


Item Type:Article
Additional Information:

Received: February 17, 2016
Published: April 7, 2016

Uncontrolled Keywords:Negishi reaction ; haloBODIPY ; BODIPY chemistry ; Palladium ; Lasers
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:44464
Deposited On:14 Sep 2017 11:17
Last Modified:14 Sep 2017 11:50

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