Efficient and practical catalyst-free-like dehydrative N-alkylation of amines and sulfinamides with alcohols initiated by aerobic oxidation of alcohols under air

Article abstract of DOI:10.1016/j.tet.2015.11.016

We developed simple and practical N-alkylation reactions of amines and sulfinamides with primary and secondary alcohols by using only catalytic amounts of air as the initiator without adding any external catalysts. This method has advantages of simple conditions, easy operation, and comparatively wider scope of substrates, providing an efficient and green catalyst-free-like alcohol-based dehydrative N-alkylation method. Mechanistic studies revealed that air initiated the reactions by aerobic oxidation of the alcohols to the key initiating aldehydes or ketones in the presence of bases.