The ability to produce heterocyclic compounds from simple starting materials is highly desirable in organic synthesis. One such heterocyclic system is indole which has particular application in pharmaceuticals. Retrosynthetically, indole-like heterocycles could be produced by the intermolecular addition-substitution tandem reaction between aniline derivatives and an alkyne. The addition product nominally generates a gold carbene intermediate that could be susceptible to nucleophilic interception by the activated aromatic ring thus promoting a cyclization via electrophilic aromatic substitution. Herein, we describe the process of optimizing reaction conditions by variations in solvent, catalyst, temperature, oxidant, and base to facilitate synthesis of the target heterocycle.

Gold-catalyzed intermolecular nucleophilic interception chemistry

251st National Meeting (2016)

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