Direct Assembly of Angular 5-5-5 Tricyclic Skeletons via a Rh(III)-Catalyzed C-H Activation/Annulation Cascade
Yanyan Li1, Yong Wang1, Huishi Wang1
1Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, State Key Laboratory of Coking Coal Resources Green Exploitation, Pingyuan Laboratory, and College of Chemistry, Zhengzhou University, Zhengzhou 450052, P. R. China.
Abstract:
Angular 5-5-5 tricyclic skeletons are privileged yet synthetically challenging motifs due to their high congestion and strain. Herein, we report a Rh(III)-catalyzed cascade annulation of azomethine imines with alkene-tethered vinyl diazo-succinimides, enabling direct access to angular 5-5-5 tricycles in up to 99% yield with excellent regioselectivity under mild reaction conditions. The transformation proceeds through directed C-H activation followed by carbene migratory insertion and an intramolecular [3 + 2] cycloaddition. A broad substrate scope and functional-group tolerance are demonstrated, providing a concise approach to densely fused angular frameworks and expanding the utility of multifunctional diazo reagents in transition-metal-catalyzed cascade synthesis.
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