Superelectrophilic Tscherniac amidomethylation of aromatics with N-hydroxymethylphthalimide in trifluoromethanesulfonic acid

Article abstract of DOI:10.1055/s-1993-26001

N-Hydroxymethylphthalimide in trifluoromethanesulfonic acid (triflic acid) reacts readily at room temperature with benzene, halo-, polyhalo- and halonitrobenzenes to give high yields of the corresponding α-amidomethylated products. The scope of the α-amidomethylation reaction is substantially extended by the studied system, which is considered to involve diprotonated N-hydroxymethylphthalimide as the de facto superelectrophilic reagent.