Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds
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
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.
diazo compounds, fluorine, hypervalent compounds, reaction mechanisms, rhodium catalyst
IdentifiersURN: urn:nbn:se:su:diva-135135DOI: 10.1002/anie.201602137ISI: 000383253300041PubMedID: 27219856OAI: oai:DiVA.org:su-135135DiVA: diva2:1043752