Thermally generated arynes (by the hexadehydro-Diels–Alder (HDDA) reaction) can undergo trapping reactions with N–heterocycles such as N–heteroaromatics (quinoline, isoquinoline and pyridine) and strained cyclic amines (diaziridines). The initially formed 1,3-zwitterionic species (a) can collapse intramolecularly to give novel 1 : 1 adducts of the heterocycle and benzyne; (b) protonate intramolecularly within the zwitterion, followed by a ring-opening event to generate hydrazones; (c) can react with an externally added, electrophilic third-component to give functionalized heterocyclic products; or (d) can react with an external protic nucleophile to produce, following collapse of the ion pair resulting from protonation of the zwitterion, a variety of three-component assemblies. Mechanisms for formation of some of the 1 : 1 adducts are supported by DFT methods. The hydrazones generated from this strategy can be used to synthesize fischer indole adducts. I will present these different modes of reactions that can be realized to construct multifunctional heterocyclic motifs and also to gain some of their mechanistic insights.

Reactions of thermally generated benzynes with N–heterocycles: Pathway and product diversity

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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