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Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 3
2016 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 29, 8410-8415 p.Article in journal (Refereed) Published
Abstract [en]

A new reaction for the rhodium-catalyzed geminal-difunctionalization-based fluorination is presented. The substrates are aromatic and aliphatic diazocarbonyl compounds. As the fluorine source a stable and easily accessible benziodoxole reagent was used. A variety of alcohol, phenol, and carboxylic acid reagents were employed to introduce the second functionality. The reaction was extended to trifluoromethylation using a benziodoxolon reagent. The fluorination and trifluoromethylation reactions probably proceed by a rhodium-containing onium ylide type intermediate, which is trapped by either the F or CF3 electrophiles.

Place, publisher, year, edition, pages
2016. Vol. 55, no 29, 8410-8415 p.
Keyword [en]
diazo compounds, fluorine, hypervalent compounds, reaction mechanisms, rhodium catalyst
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-135135DOI: 10.1002/anie.201602137ISI: 000383253300041PubMedID: 27219856OAI: oai:DiVA.org:su-135135DiVA: diva2:1043752
Available from: 2016-10-31 Created: 2016-10-31 Last updated: 2016-10-31Bibliographically approved

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Yuan, WeimingEriksson, LarsSzabó, Kálmán J.
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