Oxidative tandem annulation of 1-(2-ethynylaryl)prop-2-en-1-ones catalyzed by cooperative iodine and TBHP

Abstract

A new, metal-free I₂-catalyzed oxidative tandem annulation of 1,6-enynes by employing tert-butyl hydroperoxide (TBHP) as the oxidant and the oxygen atom resource for the synthesis of 1H-cyclopropa-[b]naphthalene-2,7-diones is developed. This reaction allows the formation of three new chemical bonds through selective radical addition across the CC bond and tandem cyclization cascades, which features a broad 1,6-enyne scope and excellent chemo- and diastereoselectivities.