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Oxidative C−C Bond Formation (Scholl Reaction) with DDQ as an Efficient and Easily Recyclable Oxidant

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journal contribution
posted on 06.08.2009, 00:00 by Linyi Zhai, Ruchi Shukla, Rajendra Rathore
DDQ in the presence of an acid is known to oxidize a variety of aromatic donors to the corresponding cation radicals. Herein, we now demonstrate that the DDQ/H+ system can be effectively utilized for the oxidative C−C bond formations or biaryl synthesis. The efficient preparation of a variety of polyaromatic hydrocarbons including graphitic hexa-peri-hexabenzocoronenes, ease of isolation of the clean products, and ready regeneration of DDQ from easily recovered reduced DDQ-H2 advances the use of DDQ/H+ for Scholl reactions.