Acid-Catalyzed Oxy-aminomethylation of Styrenes

Guillén, Marian; Liu, Sensheng; Díaz-Oviedo, C. David; Klussmann, Martin; List, Benjamin

doi:10.1021/acscatal.3c05342

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Acid-Catalyzed Oxy-aminomethylation of Styrenes

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Guillén, Marian
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Liu, Sensheng
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons268123

Díaz-Oviedo, C. David
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58702

Klussmann, Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Guillén, M., Liu, S., Díaz-Oviedo, C. D., Klussmann, M., & List, B. (2024). Acid-Catalyzed Oxy-aminomethylation of Styrenes. ACS Catalysis, 14(2), 751-756. doi:10.1021/acscatal.3c05342.

Cite as: https://hdl.handle.net/21.11116/0000-000E-43B5-A

Abstract

We report a strong Brønsted acid-catalyzed three-component oxy-aminomethylation of styrenes with sym-trioxane and sulfonamides or carbamates. This transformation provides a variety of 1,3-oxazinanes in moderate to good yields under mild reaction conditions. The obtained heterocycles can be readily transformed into the corresponding 1,3-amino alcohols, which are useful building blocks for the synthesis of pharmaceutically relevant molecules. Mechanistic studies suggest the intermediacy of an in situ formed 1,3,5-dioxazinane and a subsequent reaction with the olefin.