Tandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromides

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dc.contributor.authorBłocka, Aleksandra
dc.contributor.authorChaładaj, Wojciech
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2022-06-24T12:24:18Z
dc.date.available2022-06-24T12:24:18Z
dc.date.issued2022
dc.description.abstractWe report a new method for a tandem Pd-catalyzed intramolecular addition of active methylene compounds to internal alkynes followed by coupling with aryl and heteroaryl bromides. Highly substituted vinylidenecyclopentanes were obtained with good yields, complete selectivity, and excellent functional group tolerance. A plausible mechanism, supported by DFT calculations, involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The excellent regio- and stereoselectivity arises from the 5-exo-dig intramolecular addition of the enol form of the substrate to alkyne activated by the π-acidic Pd(II) center, postulated as the rate-determining step.en
dc.description.sponsorshipPolish National Science Centre (grant 2016/22/E/ST5/00537) Wroclaw Centre for Networking and Supercomputing (grant No. 518).
dc.identifier.citationCitation:Błocka, A.; Chaładaj, W. Tandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromides. Molecules 2022,27, 630. https://doi.org/10.3390/molecules27030630en
dc.identifier.doi10.3390/molecules27030630
dc.identifier.issn1420-3049
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21380
dc.language.isoen
dc.publisherMDPIen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectpalladiumen
dc.subjecthomogeneous catalysisen
dc.subjectalkynesen
dc.subjectcross-couplingen
dc.subjecttandem reactionsen
dc.titleTandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromidesen
dc.typearticleen
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