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Oxidative C - C bond formation (Scholl Reaction) with DDQ as an efficient and easily recyclable oxidant

by Linyi Zhai, Ruchi Shukla, Rajendra Rathore
Organic Letters ()
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Abstract

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-H(2) advances the use of DDQ/H(+) for Scholl reactions.

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