Copper-Catalyzed Silylcupration of Activated Alkynes

Dedicated to the memory of Jean Normant, a wonderful man and a truly inspiring chemist

Abstract

A highly efficient catalytic silylcupration of activated alkynes is reported. Upon reaction with silylboronates and methanol in THF at room temperature in the presence of copper(I) fluoride tris(triphenylphosphine), a range of ynamides and propiolates were found to undergo a smooth silylcupration. This reaction, which tolerates various functional groups, affords a straightforward and efficient entry to the corresponding β-silylenamides and -acrylates, which were formed with high levels of regio- and stereoselectivities.

Key words

copper catalysis - silylcupration - ynamides - propiolates - silylboronates

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