title: Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden.
authors.forename: Weiming
authors.initials: W
authors.lastname: Yuan
authors.affiliation: Department of Materials and Environmental Chemistry, Stockholm University, Sweden.
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden. kalman@organ.su.se.
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó
keywords: diazo compounds; fluorine; hypervalent compounds; reaction mechanisms; rhodium catalyst