Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-05, Vol.2015 (14), p.3069-3075
Main Authors: Pégot, Bruce, Urban, Céline, Bourne, Aaron, Le, Thanh Nghi, Bouvet, Sébastien, Marrot, Jérôme, Diter, Patrick, Magnier, Emmanuel
Format: Article
Language:English
Subjects:
Alkylation
Fluorine
Halogenation
Sulfoxides
Sulfoximines
Synthetic methods
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Summary: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. Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500201