Friedel-Crafts acylation with amides.

Friedel-Crafts acylation has been known since the 1870s, and it is an important organic synthetic reaction leading to aromatic ketone products. Friedel-Crafts acylation is usually performed with carboxylic acid chlorides or anhydrides, while amides are generally not useful substrates in these reactions. Despite being the least reactive carboxylic acid derivative, we have found a series of amides capable of providing aromatic ketones in good yields (55-96%, 17 examples).

Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles.

Experimental and theoretical studies suggest the involvement of dicationic, superelectrophilic N-acyliminium ions in conversions catalyzed by superacids.