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Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents
Author(s) -
Pégot Bruce,
Urban Céline,
Bourne Aaron,
Le Thanh Nghi,
Bouvet Sébastien,
Marrot Jérôme,
Diter Patrick,
Magnier Emmanuel
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500201
Subject(s) - electrophile , chemistry , reagent , moiety , combinatorial chemistry , electrophilic addition , electrophilic substitution , organic chemistry , catalysis
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.