A highly efficient metal-free hydrocarbonylation of alkynes with propargylamines and water

Abstract

Metal-catalyzed hydrocarbofunctionalizations of alkynes or alkenes are well established. In contrast, metal-free strategies have few precedents. We report herein a multicomponent reaction that generates functionalized 1,4-dicarbonyl motifs via formal hydrocarbonylation of activated alkynes with propargylamines and water under metal-free conditions. This novel synthesis method utilizes propargylamines and water as carbonyl and proton precursors in which propargylamines are activated in situ by alkynes for α-C(sp³)–H activation and C–N bond cleavage. This method exhibits simple and mild conditions, high efficiency, and good functional group tolerance. Meanwhile, it represents a general strategy for the merger of C–N bond activation with hydrocarbonylation of unsaturated hydrocarbons.