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

preprint
submitted on 28.05.2020 and posted on 29.05.2020 by Takuya Nagai, Nao Mimata, Yoshihiro Terada, Chikayoshi Sebe, Hiroki Shigehisa
Guided by the transition metal hydrogen atom transfer and radical-polar crossover concept, we developed a catalytic, Markovnikov-selective, functional-group tolerant, and scalable synthesis of cyclic carbamates, which are found in the structures of many bioactive compounds. This method not only provides common oxazolidinones but also six-to-eight-membered ring products. The reaction proceeds through the intramolecular displacement of an alkylcobalt(IV) in-termediate and dealkylation by 2,4,6-collidine; the activation energies of these steps were calculated by DFT. Cyclic ureas and cyclic phosphoramidates were also synthesized under the same reaction conditions.

History

Email Address of Submitting Author

cgehisa@musashino-u.ac.jp

Institution

Musashino university

Country

Japan

ORCID For Submitting Author

0000-0003-3034-1159

Declaration of Conflict of Interest

no conflict of interest

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