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Rhodium‐Catalyzed Geminal Oxyfluorination and Oxytrifluoro‐Methylation of Diazocarbonyl Compounds
Author(s) -
Yuan Weiming,
Eriksson Lars,
Szabó Kálmán J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602137
Subject(s) - trifluoromethylation , geminal , chemistry , rhodium , electrophile , reagent , ylide , catalysis , organic chemistry , combinatorial chemistry , trifluoromethyl , medicinal chemistry , alkyl
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.