An unprecedented CC double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.

Here we report a capture reaction of hexadehydro–Diels–Alder derived benzyne with various substituted oxazoles. With methyl, hydrogen or phenyl as the substituent at 2-position of oxazole, we obtained epoxyanthracene derivative and dicarbonylation on benzene ring. The reaction does not require any catalyst and additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.

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