A new arylation of silyl enol ethers by quinone monoacetal substitution

Quinone monoacetals (QMAs) were found to be convenient substrates for a unique arylation reaction of enol silyl ethers. This arylation process of QMAs typically proceeds through the acetal activation of the QMAs by a hydrogen-bond donor solvent, such as a fluoroalcohol, for the initiating step. The silyl transfer from silyl enol ethers to the carbonyl oxygen of the QMAs appears to be involved in the C-C coupling step, followed by QMA aromatization. By this method, valuable alpha-aryl carbonyl compounds containing o-phenol moieties can be obtained directly under mild conditions without lactone formation. (C) 2014 Elsevier Ltd. All rights reserved.