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Efficient Palladium-Catalyzed Aerobic Oxidative Carbocyclization to Seven-Membered Heterocycles
Stockholm University; Hunan University, Changsha, China.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm University.
2020 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 26, no 67, p. 15513-15518Article in journal (Refereed) Published
Abstract [en]

The use of molecular oxygen in palladium-catalyzed oxidation reactions is highly widespread in organic chemistry. However, the direct reoxidation of palladium by O2 is often kinetically unfavored, thus leading the deactivation of the palladium catalyst during the catalytic cycle. In the present work, we report a highly selective palladium-catalyzed carbocyclization of bisallenes to seven-membered heterocycles under atmospheric pressure of O2. The use of a homogenous hybrid catalyst (Co(salophen)-HQ, HQ=hydroquinone) significantly promotes efficient electron transfer between the palladium catalyst and O2 through a low-energy pathway. This aerobic oxidative transformation shows broad substrate scope and functional group compatibility and allowed the preparation of O-containing seven-membered rings in good yields in most cases. 

Place, publisher, year, edition, pages
2020. Vol. 26, no 67, p. 15513-15518
Keywords [en]
aerobic oxidation, carbocyclization, heterocycles, palladium, regioseletivity
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-40332DOI: 10.1002/chem.202004265ISI: 000581739700001Scopus ID: 2-s2.0-85092889492OAI: oai:DiVA.org:miun-40332DiVA, id: diva2:1480861
Available from: 2020-10-27 Created: 2020-10-27 Last updated: 2021-05-04

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Bäckvall, Jan-Erling

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CiteExportLink to record
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