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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 ()

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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