Recently, our research group has developed several new Ti-catalyzed reactions that hinge on a unique Ti(II)/Ti(IV) redox cycle which can cleave the N=N bond in diazenes such as azobenzene, and deliver the resulting nitrene fragment to a variety of different organic substrates. In this talk, our work into the design of several new multicomponent oxidative nitrene transfer reactions will be discussed. For example, we have demonstrated that this Ti redox catalytic manifold is capable of formal [2+2+1] cyclizations of alkynes with nitrenes to form pyrroles, the multicomponent oxidative coupling of alkynes with alkenes and nitrenes to form a,b-unsaturated imines or iminocyclopropanes, or performing arrested McMurry coupling reactions to form epoxides. In addition, insight from mechanism will be used to provide a rationale for the design catalysts that improve regio- and chemoselectivity of these reactions.

Recent advances in Ti-catalyzed nitrene transfer reactions

253rd National Meeting (2017)

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