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Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization-Carbonylation-Alkynylation
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-6604-6173
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2016 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 42, p. 13846-13849Article in journal (Refereed) Published
Abstract [en]

A highly selective cascade reaction that allows the direct transformation of dienallenes to spirocyclobutenes (spiro[3.4]octenes) as single diastereoisomers has been developed. The reaction involves formation of overall four C-C bonds and proceeds-via a palladium-catalyzed oxidative transformation with insertion of olefin, olefin, and carbon monoxide. Under slightly different reaction conditions, an additional CO insertion takes place to give spiro[4.4]nonenes with formation of overall five C-C bonds.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 138, no 42, p. 13846-13849
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-136928DOI: 10.1021/jacs.6b09240ISI: 000386540500021OAI: oai:DiVA.org:su-136928DiVA, id: diva2:1061670
Funder
EU, European Research CouncilSwedish Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg FoundationAvailable from: 2017-01-03 Created: 2016-12-19 Last updated: 2022-02-28Bibliographically approved

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Qiu, YouaiYang, BinZhu, CanBäckvall, Jan-E.

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