Dual Palladium/Copper-Catalyzed <i>anti</i>-Selective Intermolecular Allenylsilylation of Terminal Alkynes: Entry to (<i>E</i>)-Silyl Enallenes
Liangfeng Yang, Qiuan Wang, Jin‐Heng Li
Abstract
A palladium-/copper-cocatalyzed three-component trans-allenylsilylation of terminal alkynes with propargyl acetates and PhMe2SiBpin is described, which is driven by the regioselective allenylation of the alkyne with propargyl acetates and then silylation. This method allows the simultaneous incorporation of an allene and silicon across the C≡C bond and provides a highly chemo-, regio-, and stereoselective alkyne difunctionalization route to the synthesis of valuable (E)-silyl enallenes. The utility of this method is highlighted by late-stage derivatization of bioactive compounds.
Topics & Concepts
PropargylAlkyneChemistrySilylationRegioselectivityAlleneDerivatizationCatalysisPalladiumCopperStereoselectivityCombinatorial chemistryIntermolecular forceMedicinal chemistryOrganic chemistryMoleculeHigh-performance liquid chromatographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCatalytic Cross-Coupling Reactions