Molybdenum-Catalyzed Intermolecular Deoxygenative Cross-Coupling Reactions of 1,2-Diketones with α-Ketoamides

Abstract

Here we describe the Mo-catalyzed intermolecular deoxygenative cross coupling of the bench stable and readily accessible1,2-diketones with α-ketoamides, in which three of the four carbonyl oxygen atoms were eliminated along with the formations of a carbon–nitrogen bond and a carbon–carbon double bond in one step under Mo-catalysis. Various pyrrol-2-ones were secured in up to 96% yield by utilizing a commercial Mo-catalyst. The synthetic potential of the current methodology is additionally demonstrated by synthetic transformations, a gram-scale synthesis, and derivatization of several natural products and drug molecules. The preliminary mechanistic investigation suggest this cascade process might be initiated via the formal intermolecular N–H insertion and followed by the intramolecular carbonyl–carbonyl olefination reaction, in which both steps were catalyzed by a single Mo-catalyst.