Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides

Ulrich Kloeckner, Boris J. Nachtsheim
2014 Chemical Communications  
An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO 2 -source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under very mild reaction conditions, the desired mononitrated aryl sulfonamides were isolated in up to 87% yield. This is the first example of an iodane-mediated oxidative nitration. Scheme 2 Substrate scope. Reaction conditions: 0.2 mmol 1a, 0.24 mmol NaNO 2
more » ... a, 0.24 mmol NaNO 2 , 0.24 mmol PIFA in acetonitrile at rt. Reaction time: 1-48 h. Communication ChemComm
doi:10.1039/c4cc04738a pmid:25068377 fatcat:xycr3z2cz5hf3n3tlzmb6eyrmq