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Synfacts 2009(10): 1104-1104
DOI: 10.1055/s-0029-1217929
DOI: 10.1055/s-0029-1217929
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Method for Oxidative C-C Bond Formation
L. Zhai, R. Shukla, R. Rathore*
Marquette University, Milwaukee, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. September 2009 (online)
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.