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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.

SUBMITTER: Yuan W

PROVIDER: S-EPMC5089581 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.

Yuan Weiming W Eriksson Lars L Szabó Kálmán J KJ

Angewandte Chemie (International ed. in English) 20160524 29

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 p ...[more]

PMID: 27219856

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