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

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.