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Modular Access to <i>N</i>-SF<sub>5</sub> Azetidines.

ABSTRACT: A general and modular strategy has been developed for the synthesis of N-SF5 azetidines, a new class of scaffolds with potential utility in medicinal chemistry. This transformation leverages bench-stable and scalable SF5-transfer reagents to generate the SF5 radical, which engages azabicyclo[1.1.0]butanes bearing ketone, ester, alkyl, or aryl substituents in strain-release difunctionalization reactions. The method proceeds under mild reaction conditions, features broad functional group tolerance, and offers operational simplicity. The resulting N-SF5 azetidines demonstrate high aqueous stability and increased lipophilicity, positioning them as a novel class of potential bioisosteres in medicinal chemistry.

SUBMITTER: Li R 

PROVIDER: S-EPMC12443333 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature

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Modular Access to &lt;i&gt;N&lt;/i&gt;-SF&lt;sub&gt;5&lt;/sub&gt; Azetidines.

Li Renzhe R   Hu Chao C   Liu Chang C   Lyness Thomas T   Li Wenyuan W   Cai Chen-Yan CY   Crossley Eric E   Kanda Yuzuru Y   Merchant Rohan R RR   Matsuura Bryan S BS   Williams Noelle S NS   Qin Tian T  

Journal of the American Chemical Society 20250912 38

A general and modular strategy has been developed for the synthesis of <i>N</i>-SF<sub>5</sub> azetidines, a new class of scaffolds with potential utility in medicinal chemistry. This transformation leverages bench-stable and scalable SF<sub>5</sub>-transfer reagents to generate the SF<sub>5</sub> radical, which engages azabicyclo[1.1.0]butanes bearing ketone, ester, alkyl, or aryl substituents in strain-release difunctionalization reactions. The method proceeds under mild reaction conditions, f  ...[more]

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