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Mechanism of Au(III)-Mediated Alkoxycyclization of a 1,6-Enyne
Norwegian Univ Sci & Technol, Dept Chem, Hogskoleringen 5, N-7491 Trondheim, Norway.
Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary.ORCID iD: 0000-0002-4150-477X
Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary.ORCID iD: 0000-0002-4978-0365
Norwegian Univ Sci & Technol, Dept Chem, Hogskoleringen 5, N-7491 Trondheim, Norway.
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2019 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 141, no 45, p. 18221-18229Article in journal (Refereed) Published
Abstract [en]

Gold-mediated homogeneous catalysis is a powerful tool for construction of valuable molecules and has lately received growing attention. Whereas Au(I)-catalyzed processes have become well established, those mediated by Au(III) have so far barely been explored, and their mechanistic understanding remains basic. Herein, we disclose the combined NMR spectroscopic, single-crystal X-ray crystallographic, and computational (DFT) investigation of the Au(III)-mediated alkoxycyclization of a 1,6-enyne in the presence of a bidentate pyridine-oxazoline ligand. The roles of the counterion, the solvent, and the type of Au(III) complex have been assessed. Au(III) is demonstrated to be the active catalyst in alkoxycyclization. Alkyne coordination to Au(III) involves decoordination of the pyridine nitrogen and is the rate-limiting step.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2019. Vol. 141, no 45, p. 18221-18229
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Organic Chemistry Physical Chemistry
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URN: urn:nbn:se:uu:diva-400015DOI: 10.1021/jacs.9b09108ISI: 000498281600035PubMedID: 31618010OAI: oai:DiVA.org:uu-400015DiVA, id: diva2:1380991
Available from: 2019-12-19 Created: 2019-12-19 Last updated: 2020-01-09Bibliographically approved

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Erdélyi, Máté

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