Abstract
A (3 + 2) annulation of allenyl- and, after rapid isomerization, propargylsilanes with internal 1-aryl-1-alkynes to form 4-methylenecyclopentenes is reported. The reaction is initiated by a silylium ion, and the catalytic cycle is subsequently maintained by the self-regeneration of the silylium-ion promoter. Unlike the well-established Danheiser annulation, where the allenylsilane serves as a three-carbon synthon, the present transformation engages the allenylsilane as a two-carbon synthon. Experimental observations and DFT calculations unveil a reaction cascade involving various β-silicon-stabilized carbocations, where a pentadienyl-to-allyl cation electrocyclization is the key step.
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