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

Linyi Zhai; Ruchi Shukla; Rajendra Rathore

doi:10.1021/ol901331p

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

Org Lett. 2009 Aug 6;11(15):3474-7. doi: 10.1021/ol901331p.

Authors

Linyi Zhai¹, Ruchi Shukla, Rajendra Rathore

Affiliation

¹ Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201, USA.

PMID: 19594139
DOI: 10.1021/ol901331p

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.