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Guided by the transition-metal hydrogen atom transfer and radical-polar crossover concepts, we developed a functional-group-tolerant and scalable method for the synthesis of cyclic carbamates and ureas, which are found in the structures of bioactive compounds. This method provides not only a common five-membered ring but also six-to-eight-membered ring products. The reaction proceeds through the intramolecular displacement of an alkylcobalt(IV) intermediate and dealkylation by 2,4,6-collidine; the activation energies of these steps were calculated by DFT.

Catalytic Dealkylative Synthesis of Cyclic Carbamates and Ureas via Hydrogen Atom Transfer and Radical-Polar Crossover