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Palladium-Catalyzed Oxidative Domino Carbocyclization-Arylation of Bisallenes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 2
2016 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 6, no 10, 6398-6402 p.Article in journal (Refereed) Published
Abstract [en]

Herein we report a highly efficient and site selective palladium-catalyzed oxidative carbocyclization arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the solvent proved to be crucial for the selectivity and the reactivity displayed. Interestingly, in the absence of the nucleophile, an oxidative carbocyclization-beta-elimination pathway predominates. The reaction conditions are compatible with a wide range of functional groups, and the reaction exhibits broad substrate scope. Furthermore, key information regarding the mechanism was obtained using control experiments and kinetic studies.

Place, publisher, year, edition, pages
2016. Vol. 6, no 10, 6398-6402 p.
Keyword [en]
bisallenes, palladium catalysis, carbocyclization, oxidation, arylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-136151DOI: 10.1021/acscatal.6b02070ISI: 000385057900010OAI: oai:DiVA.org:su-136151DiVA: diva2:1050778
Available from: 2016-11-30 Created: 2016-11-29 Last updated: 2016-11-30Bibliographically approved

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Bäckvall, Jan-E.
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