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Copper-Catalyzed Direct SulfoximinationContributor(s):Paul Knochel, Thomas Kunz
Osaka University, Japan and RWTH Aachen University, Germany
Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions
Org. Lett. 2011, 13: 359-361
18 March 2011 (online)
C-H activation - sulfoximination - copper
Herein, the direct dehydrogenative sulfoximination of azoles and polyfluoroarenes is reported. This copper acetate catalyzed C-N coupling proceeds effectively at room temperature in air and affords a wide range of N-arylsulfoximines in excellent yield. With this protocol, a preactivation step, such as halogenation or the formation of a metalated species, is not necessary.
The use of other copper salts gave similar or slightly inferior results. The addition of different ligands leads to decreasing yields. For a full conversion the combination of the phosphate base and DMF was necessary. Using an enantiopure sulfoximine gave the desired product maintaining the enantiomeric excess.