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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, 05:29 and posted on 29.05.2020, 09:49 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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