Azetidines are four-membered nitrogen-containing heterocycles that have recently gained considerable interest as building blocks for complex drug scaffolds. An efficient approach to access azetidines is via photochemical [2+2]-cycloadditions, which have historically been used for the synthesis of cyclobutanes and oxetanes but have remained limited for azetidines. Recently, important developments in this area have significantly expanded the utility and scope of the aza Paternò-Büchi reaction, including intermolecular and intramolecular visible light-mediated [2+2]-cycloadditions using cyclic oximes as imine equivalents. These methodologies exploit the unique triplet state reactivity of oximes by proceeding via a triplet energy transfer (EnT) mechanism. However, the requirement of cyclic oxime precursors necessitates further exploration of oxime reactivity. Herein, we report expansion of the scope of oxime reactivity for visible light-mediated aza Paternò-Büchi reactions.

Synthesis of azetidines via visible light-mediated [2+2]-cycloadditions

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