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Org Biomol Chem. 2013 Apr 21;11(15):2460-5. doi: 10.1039/c3ob27351b. Epub 2013 Feb 21.

Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity.

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  • 1Department of Chemistry, Northeast Normal University, Changchun 130024, China.


NBS-mediated addition-elimination reaction of sulfonamides/carboxamides and formamides afforded N-sulfonylamidines and N-formylarylamides, respectively, depending on the different mechanism of elimination. Hydrogen bond-induced proton transfer leads to enhanced reactivities and was proposed as the key driving force for the reaction to take place. The protocol demonstrates the possibility of constructing chemical bonds based on a proton transfer strategy induced by noncovalent hydrogen bond interaction.

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