Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones

A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations suggest that the reaction proceeds through a one-electron process involving free radical species in which PhBr acts as the oxidant.