At ambient temperature, deprotonated sulfoximines react with 1-trifluoromethylalkenes to provide either N-or C-gemdifluoroalkenylated products. The reaction site depends upon the N substituent of the starting material. The optimal conditions involve the use of a superbasic system NaOH in dimethyl sulfoxide. The reactions are characterized by a broad substrate scope and medium to high yields. Scale-up experiments of both the N-and C-gem-difluoroalkenylations proceeded well. Treatment of a Ndifluoroallyl sulfoximine with an aryl thiol under dioxygen afforded the corresponding oxygenated addition product.
α,β-Unsaturated phosphine sulfides may exhibit different reactivity from α,β-unsaturated phosphine oxides toward nucleophilic addition and thus may find new applications in copper(I)-catalyzed asymmetric reactions. Herein, various α,β-unsaturated phosphine sulfides were prepared in moderate to excellent yields from the parent α,β-unsaturated phosphine oxides with Lawesson’s reagent. The reaction enjoys a broad substrate scope and tolerates a variety of functional groups.
N-Alkyl sulfoximines react with arynes generated in situ under mild conditions providing o-sulfinylanilines in good yields. The transformation is characterized by a broad substrate scope and a good functional group tolerance. The structure of a reaction product was confirmed by single-crystal X-ray diffraction.Note pubs.acs.org/joc
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