An Efficient Method for Oxidative C-C Bond Formation

Significance

The Scholl reaction involves the ­oxidative cyclodehydrogenation of aromatic rings linked by one bond to form fused polyaromatic ­hydrocarbons. The reaction is generally performed using a metal oxidant such as ferric chloride (FeCl₃) or can occur electrochemically. There are drawbacks to the FeCl₃ oxidation, including the necessity of a large excess of oxidant and some chlorination of aromatic products. The authors demonstrate a straightforward procedure using dichlorodicyano-p-benzoquinone (DDQ) as a stoichiometric and recyclable oxidant in the presence of acid.