TEMPO-Mediated Synthesis of Indolyl/Imidazo[1,2-a]pyridinyl-Substituted para-Quinone Methides from Butylated Hydroxytoluene.

A series of indolyl or imidazo[1,2-a]pyridinyl-substituted para-quinone methides (p-QMs) is prepared by a metal-free, TEMPO-mediated cross-dehydrogenative coupling of butylated hydroxytoluene (BHT) with indoles or imidazo[1,2-a]pyridines in good to high yields. Broad substrate scope with respect to indoles and imidazo[1,2-a]pyridines, good functional group tolerance, and acid/base-free conditions are advantageous feature of the developed protocol. The method was amenable for scale-up on the gram scale. Based on control experiments, a reaction mechanism is proposed to describe this transformation.