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Mechanisms of Rh-Catalyzed Oxyaminofluorination and Oxyaminotrifluoromethylthiolation of Diazocarbonyl Compounds with Electrophilic Reagents
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8487-1417
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-9349-7137
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 32018 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 21, p. 6646-6649Article in journal (Refereed) Published
Abstract [en]

Density functional theory calculations were performed to study the detailed reaction mechanisms of rhodium-catalyzed oxyaminofluorination and oxyaminotrifluoromethylthiolation of diazocarbonyl compounds with electrophilic N-F and N-SCF3-based reagents. The calculations show that the operating mechanisms for the two reactions are identical. The catalytic cycle starts with N-2 dissociation to provide a rhodium-carbene intermediate, followed by nucleophilic attack of tetrahydrofuran on the carbene and a rhodium coordination change generating a rhodium-enolate intermediate. Subsequent electrophilic attack introduces the fluorine or the SCF3 moiety, and it is followed by nucleophilic attack of the remaining amino group to yield the final product.

Place, publisher, year, edition, pages
2018. Vol. 20, no 21, p. 6646-6649
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-162755DOI: 10.1021/acs.orglett.8b02628ISI: 000449443100008PubMedID: 30350651OAI: oai:DiVA.org:su-162755DiVA, id: diva2:1274861
Available from: 2019-01-03 Created: 2019-01-03 Last updated: 2019-01-03Bibliographically approved

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Khanh Mai, BinhSzabó, Kálmán J.Himo, Fahmi
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