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Copper-Catalyzed Si–H Bond Insertion Reaction of <i>N</i>-Propargyl Ynamides with Hydrosilanes

En‐He Huang, Yingqi Zhang, Da-Qiu Cui, Xin‐Qi Zhu, Xiao Li, Long‐Wu Ye

2021Organic Letters15 citationsDOI

Abstract

Transition-metal-catalyzed Si–H bond insertion reactions are generally limited to stabilized diazo compounds. An efficient copper-catalyzed Si–H bond insertion reaction of N-propargyl ynamides with hydrosilanes is described, allowing practical and atom-economic construction of valuable organosilanes in generally moderate to excellent yields under mild reaction conditions. Notably, this reaction constitutes a new method of Si–H bond insertion reaction involving vinyl cations as key intermediates.

Topics & Concepts

ChemistryPropargylCatalysisInsertion reactionDiazoMedicinal chemistryCopperTriple bondReaction conditionsCombinatorial chemistryPolymer chemistryDouble bondOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods
Copper-Catalyzed Si–H Bond Insertion Reaction of <i>N</i>-Propargyl Ynamides with Hydrosilanes | Litcius