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- Title
Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro- Methylation of Diazocarbonyl Compounds.
- Authors
Weiming Yuan; Eriksson, Lars; Szabó, Kâlmân J.
- Abstract
A new reaction for the rhodium-catalyzed geminaldifunctionalization- 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.
- Subjects
CARBONYL compounds; FLUORINATION; METHYLATION; RHODIUM catalysts; ONIUM ions; CARBOXYLIC acids
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 29, p8410
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201602137