Ruthenium-Catalyzed Formation of 1-Azetines via Oxidative β-Elimination from Azetidine Benzoates

Azetidines and azetines, four-membered nitrogen-containing heterocycles, exhibit unique properties such as low lipophilicity and rigidity, making them promising scaffolds in pharmaceutical design and as synthetic building blocks. However, challenges in their synthesis, particularly azetines, have limited accessibility, hindering the exploration of their applications. Our innovative approach described herein involves a ruthenium-catalyzed oxidative elimination, utilizing a hydroxylamine substituent on the azetidine nitrogen. This method offers milder conditions, enabling the synthesis of 1-azetines from 22 azetidines in yields up to 99%.