Rhodium‐Catalyzed Geminal Oxyfluorination and Oxytrifluoro‐Methylation of Diazocarbonyl Compounds
2016; Wiley; Volume: 55; Issue: 29 Linguagem: Inglês
10.1002/anie.201602137
ISSN1521-3773
AutoresWeiming Yuan, Lars Eriksson, Kálmán J. Szabó,
Tópico(s)Inorganic Fluorides and Related Compounds
ResumoAbstract 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 CF 3 electrophiles.
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