Friedel-Crafts alkylation of aromatics with vinyl amides and enamides has been studied in strong acids such as trifluoromethanesulfonic acid. Depending on the nature of amides and pathway of addition, direct synthesis of the corresponding aryl amides has been achieved. The reaction of a,�-unsaturated amides such as acrylamide (1  ) occured through conjugate addition, whereas, the reaction of enamides such as N-vinyl acetamide (2  ) went through Markovnikov-type addition. The observed reactivity of these amides towards arenes can be attributed to protosolvation and the possible formation of dicationic intermediates in the superacidic medium.                                                 

Friedel-Crafts alkylation of arenes with vinyl amides and enamides: Direct synthesis of arylamides

243rd National Meeting (2012)

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