Synfacts 2011(4): 0421-0421  
DOI: 10.1055/s-0030-1259608
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Direct Sulfoximination

Rezensent(en):Paul Knochel, Thomas Kunz
M. Miyasaka, K. Hirano, T. Satoh, R. Kowalczyk, C. Holm*, M. Miura*
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  
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18. März 2011 (online)


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.