Metal-Free Oxidative Decarbonylative [3+2] Annulation of Terminal Alkynes with Tertiary Alkyl Aldehydes toward Cyclopentenes.

Abstract

A new metal-free oxidative decarbonylative [3+2] annulation of terminal alkynes with tertiary alkyl aldehydes is presented, which features broad substrate scope and excellent selectivity. The selectivity of this reaction toward cyclopentenes and indenes relies on the nature of the aldehyde substrates. While treatment of tertiary γ,δ-unsaturated aldehydes with common terminal alkynes assembles cyclopentenes, 2-methyl-2-arylpropanals succeed in accessing indenes.