An unprecedented [3+2] cycloaddition between N-tert-butanesulfinyl imines and arynes provides a stereoselective method for the synthesis of cyclic sulfoximines. Not only does the difluoro(phenylsulfonyl)methyl group play an important role in facilitating the cycloaddition reaction, it can also be removed or substituted through the transformation of the difluorinated cyclic sulfoximines to cyclic sulfinamides.
A simple and efficient palladium-catalyzed amidation-hydrolysis reaction has been developed to afford N-aryl monosubstituted carboxamides in good to excellent yields from easily accessible ketone-derived gem-dihaloolefins and aryl amines.
Copper-mediated (phenylsulfonyl)difluoromethylation of propargyl chlorides and alkynyl halides with PhSO 2 CF 2 TMS reagent was successfully achieved to give PhSO 2 CF 2 -containing allenes and alkynes, respectively. It is believed that the in situ formed PhSO 2 CF 2 Cu species is involved in the present (phenylsulfonyl)difluoromethylation reactions.
Two unprecedented and complementary synthetic strategies for S-and C-difluoromethylation of 2-substituted benzothiazoles have been developed by taking advantage of the remarkably different reactivity of CF 2 H − and 2-PySO 2 CF 2 − nucleophiles. A variety of structurally diverse difluoromethyl 2-isocyanophenyl sulfides and 2-difluoromethylated benzothiazoles were synthesized with these two new synthetic protocols.
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