A mild, expedient, one-pot trifluoromethanesulfonic anhydride mediated synthesis of N-arylimidates |
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Authors: | Mehdi Ghandi Saleh SalahiMohammad Hasani |
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Institution: | School of Chemistry, College of Science, University of Tehran, Tehran, PO Box 14155 6455, Iran |
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Abstract: | The direct transformation of various secondary amides into N-arylimidates via mild electrophilic amide activation with trifluoromethanesulfonic anhydride (Tf2O) in the presence of 2-chloropyridine (2-ClPyr) is described. Low-temperature amide activation followed by C-O bond formation with 2-naphthol provides the desired N-arylimidates in short overall reaction times. In contrast, reaction with oxindole proceeds via formation of a C-C bond to give 1-(1H-indol-2-yl)naphthalene-2-ol. |
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