A Brønsted Acid Catalyzed Redox Arylation

• Published in: Angewandte Chemie (International ed.) Vol. 53; no. 33; pp. 8718 - 8721
• Main Authors: Peng, Bo, Huang, Xueliang, Xie, Lan-Gui, Maulide, Nuno
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 11.08.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Brønsted acid catalysis; Chemistry; Chemistry, Multidisciplinary; oxazolidinones; Physical Sciences; redox reactions; Science & Technology; sulfoxides; ynamides; ELECTROPHILIC REARRANGEMENTS; ORGANIC-SYNTHESIS; ALPHA-ARYLATION; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; C-H FUNCTIONALIZATION; NUCLEOPHILIC ORTHO-ALLYLATION; Bronsted acid catalysis; redox reactions; ynamides; SAUCY-MARBET REARRANGEMENT; sulfoxides; oxazolidinones; CLAISEN REARRANGEMENT SEQUENCE; METAL-FREE; Brønsted acid catalysis
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201310865

A Brønsted acid catalyzed redox arylation of ynamides that employs aryl sulfoxides as the arylating agents is reported. This metal‐free transformation proceeds at room temperature and efficiently affords α‐arylated oxazolidinones in a redox‐neutral, atom‐economic fashion. Playing a neutral game: A Brønsted acid catalyzed redox‐neutral arylation of ynamides with aryl sulfoxides is described. A broad range of ynamides were converted into the corresponding α‐arylated oxazolidinones in good to excellent yields under mild conditions and in an atom‐economic fashion. Tf=trifluoromethylsulfonyl.