A reaction of this type can also occur between oxalyl chloride and indole, whose product can be hydrolyzed to a carboxylic acid.
A reaction related to this occurs with copper iodide as a catalyst and uses carbon monoxide to produce benzaldehyde, while another can couple two arenes. Those reactions, Gatterman-Koch and Scholl, use the same catalyst that is the hallmark of this class of reactions. A reaction of this type can also occur between oxalyl chloride and indole, whose product can be hydrolyzed to a carboxylic acid. In the more common variety, a Clemmensen reduction can be used to reduce the carbonylated product, providing an alternative to reacting with alkyl halides where overalkylation could occur. For 10 points, give this class of reactions that use a Lewis acid like aluminum chloride to either acylate or alkylate an aromatic system like benzene.
A reaction related to this occurs with copper iodide as a catalyst and uses carbon monoxide to produce benzaldehyde, while another can couple two arenes.
{Friedel-Crafts} reaction