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Palladium‐Catalyzed Carbonylative Multicomponent Fluoroalkylation of 1,3‐Enynes: Concise Construction of Diverse Cyclic Compounds

Chang‐Sheng Kuai, Bing‐Hong Teng, Xiao‐Feng Wu

2023Angewandte Chemie International Edition42 citationsDOIOpen Access PDF

Abstract

Multicomponent reactions, particularly those entailing four or more reagents, have presented a longstanding challenge due to the inherent complexities associated with balancing reactivity, selectivity, and compatibility. In this study, we describe a palladium-catalyzed multi-component fluoroalkylative carbonylation of 1,3-enynes. A series of products featuring three active functional groups-allene, fluoroalkyl, and carboxyl, were efficiently and selectively integrated in a single chemical operation. Furthermore, more intricate fluoroalkyl-substituted pyrimidinones can be constructed by simply altering the 1,3-bisnucleophilic reagent. This approach also provides a valuable strategy for the late-stage modification of naturally occurring molecules and concise construction of diverse cyclic compounds.

Topics & Concepts

PalladiumCatalysisChemistryCombinatorial chemistryOrganic chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
Palladium‐Catalyzed Carbonylative Multicomponent Fluoroalkylation of 1,3‐Enynes: Concise Construction of Diverse Cyclic Compounds | Litcius