Hydroamination is an atom-economical method to produce alkylamines, including N-heterocyclic species. The combination of an amine and an electron-rich unsaturated bond has a high energetic barrier, and a variety of catalysts have been utilized to overcome it. A Zr-based CCC N-heterocyclic pincer carbene has successfully catalyzed the production of five- and six-membered rings with various substituents. Plausible mechanisms for this reaction have been studied using density functional theory calculations. Cycloaddition, insertion, and concerted-type cyclization mechanisms will be compared. The effects of halogen ligands and substrate substitution will also be discussed.

Mechanistic studies of intramolecular hydroamination of alkylamines by a zirconium(IV) CCC-NHC pincer complex

247th National Meeting (2014)

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