A Cu-catalyzed addition of silicon or boron nucleophiles to vinylidene cyclopropanes is reported. The reactions generated propargylic silane or boron products by forming a C-Si or C-B bond at the terminal carbon of the allene moiety of vinylidene cyclopropanes. The obtained silicon and boron reagents are versatile intermediates that can undergo a variety of transformations to give synthetically useful products. Preliminary mechanistic studies indicated a copper enolate was involved in the reaction process.
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