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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dc.contributor.authorPalao Utiel, Eduardo
dc.contributor.authorDurán Sampedro, Gonzalo
dc.contributor.authorMoya Cerero, Santiago De La
dc.contributor.authorMadrid, Miriam
dc.contributor.authorGarcía López, Carmen
dc.contributor.authorRodríguez Agarrabeitia, Antonia
dc.contributor.authorVerbelen, Bram
dc.contributor.authorDehaen, Wim
dc.contributor.authorBoens, Nöel
dc.contributor.authorOrtiz García, María Josefa
dc.date.accessioned2023-06-18T05:49:13Z
dc.date.available2023-06-18T05:49:13Z
dc.date.copyright© 2016 American Chemical Society Received: February 17, 2016 Published: April 7, 2016
dc.date.issued2016-05-06
dc.description.abstractThe 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.en
dc.description.departmentDepto. de Química Orgánica
dc.description.departmentSección Deptal. de Química Orgánica (Óptica y Optometría)
dc.description.facultyFac. de Ciencias Químicas
dc.description.facultyFac. de Óptica y Optometría
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades (España)
dc.description.sponsorshipMinisterie voor Wetenschapsbeleid (Bélgica)
dc.description.statuspub
dc.eprint.idhttps://eprints.ucm.es/id/eprint/44464
dc.identifier.doi10.1021/acs.joc.6b00350
dc.identifier.issn0022-3263 (Print) 1520-6904(Online)
dc.identifier.officialurlhttps://doi.org/10.1021/acs.joc.6b00350
dc.identifier.relatedurlhttp://pubs.acs.org/doi/abs/10.1021/acs.joc.6b00350
dc.identifier.relatedurlhttps://www.ncbi.nlm.nih.gov/pubmed/27055068
dc.identifier.urihttps://hdl.handle.net/20.500.14352/23410
dc.issue.number9
dc.journal.titleJournal of Organic Chemistry
dc.language.isoeng
dc.page.final3710
dc.page.initial3700
dc.publisherACS
dc.publisherAmiceran Chemical Society
dc.relation.projectIDMAT2014-51937-C3-2-P
dc.relation.projectIDMAT2015-68837-REDT
dc.rights.accessRightsrestricted access
dc.subject.cdu547.1
dc.subject.cdu544.478
dc.subject.keywordNegishi reaction
dc.subject.keywordhaloBODIPY
dc.subject.keywordBODIPY chemistry
dc.subject.keywordPalladium
dc.subject.keywordLasers
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco2306 Química Orgánica
dc.titleExploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyesen
dc.typejournal article
dc.volume.number81
dspace.entity.typePublication
relation.isAuthorOfPublication7940c6e8-25c3-4083-b533-0c34e155dfa8
relation.isAuthorOfPublication0486160c-3df6-4270-bf91-3e96cd33d85d
relation.isAuthorOfPublication07f337af-8a30-4929-81db-4e92176e5c87
relation.isAuthorOfPublication.latestForDiscovery0486160c-3df6-4270-bf91-3e96cd33d85d
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