ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
intermolecular-azetidines-chemrxiv.pdf (1.42 MB)
0/0

Synthesis of Azetidines via Visible Light-Mediated Intermolecular [2+2] Photocycloaddition

preprint
submitted on 10.02.2020 and posted on 11.02.2020 by Marc R. Becker, Emily R. Wearing, Corinna Schindler

Intermolecular [2+2] photocycloadditions represent a powerful method for the synthesis of highly strained, four-membered rings. While this approach is commonly employed for the synthesis of oxetanes and cyclobutanes, the synthesis of azetidines via intermolecular aza Paternò-Büchi reactions remains highly underdeveloped. Herein we report a visible light-mediated intermolecular aza Paternò-Büchi reaction that utilizes glyoxylate oximes as reactive intermediates activated via triplet energy transfer. This approach is characterized by its operational simplicity, mild conditions and broad scope, and allows for the synthesis of highly functionalized azetidines from readily available precursors.

Funding

David and Lucile Packard Foundation, Alfred P. Sloan Foundation, Camille and Henry Dreyfus Foundation

History

Email Address of Submitting Author

marcrb@umich.edu

Institution

University of Michigan, Ann Arbor

Country

United States

ORCID For Submitting Author

0000-0003-4259-6992

Declaration of Conflict of Interest

The authors declare no competing interests.

Exports