Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents. Issue 14 (26th March 2015)

• Record Type: Journal Article
• Authors: Pégot, Bruce; Urban, Céline; Bourne, Aaron; Le, Thanh Nghi; Bouvet, Sébastien; Marrot, Jérôme; Diter, Patrick; Magnier, Emmanuel
• Is Part Of: European journal of organic chemistry. Issue 14(2015)
• Page Start: 3069
• Page End: 3075
• Publication Date: 2015-03-26
• Subjects: Synthetic methods -- Halogenation -- Alkylation -- Fluorine -- Sulfoximines -- Sulfoxides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500201
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient and convenient method is described that allows the synthesis of a set of difluoromethyl sulfoximines, as well as chlorofluoromethyl sulfoxides, sulfones, and sulfoximines. Our procedure does not require metals or nonrecommended freons, and it gives rise to an original route to Hu's reagent. Unprecedented chlorofluoromethyl sulfoximines have been also isolated, and these compounds have been shown to act as an electrophilic source of this original bis‐halogenated moiety. The mechanism of the electrophilic chlorofluoromethylation is also discussed. Abstract : Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.