Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas

Acetylene gas isan important feedstock for chemical production,although it is underutilized in organic synthesis. We have developedan intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanesby a stereospecific aryloxycyclization through the nucleophilic regioselectiveopening of cyclopropyl gold(I)-carbene intermediates. The syntheticapplication of this method was demonstrated in the late-stage functionalizationof the natural product lapachol.

Automated summary

In this study, a new method was developed for the reaction of acetylene gas with o-allylphenols, resulting in the formation of chromanes through nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the natural product lapachol.