One of the most challenging goals of modern synthetic chemistry is to develop a single-step reaction to build useful complex molecules from simple reactants. We report a triple aryne-tetrazine (TAT) reaction that enables rapid access to a new class of polyaromatic heterocycles, dibenzo[de,g]cinnoline. This new reaction utilizes simple tetrazine and aryne starting materials, proceeds in a single operation, and takes less than 5 minutes in air with no metal catalyst. Focusing on elucidation of each mechanistic step, we provides the first mechanistic observation for TAT reaction with isolation and characterization of several intermediates and byproducts, deuterium exchange experiments, crossover experiments between two competitive reactions, and DFT calculations of ground state energies of isomers. This mechanistic study allows to have insight into aryne chemistry instead of limiting it to perspective of TAT reaction.

Discovery and mechanistic study of triple aryne-tetrazine reaction enabling rapid access to a new class of polyaromatic heterocycles

251st National Meeting (2016)

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