O-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles

Abstract

Indole scaffolds, which are important structural motifs in organic chemistry, have garnered sustained interest due to their prevalence in pharmaceuticals, agrochemicals, and natural products. This study establishes a novel umpolung activation strategy for γ-position functionalization of electron-poor alkenyl sulfoxides, generating allylidenesulfonium intermediates that are subsequently trapped by indoles, achieving the synthesis of 3-functionalized indoles. Further transformations and plausible mechanism were investigated.