ArticleACS catalysis2026
Skeletal Rearrangement of Biaryls via Rhodium-Azirine Intermediate: A Route to Solid-State Emissive Polycyclic Sulfamates.
Article in ACS catalysis, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
We report a rhodium-catalyzed cascade transformation of biaryl alkynylsulfamates that enables access to rigid, spirocyclic cycloheptatrienes with strong solid-state fluorescence. Building on prior work confirming selective 7-endo nitrene-alkyne cyclization, our design leverages skeletal rigidity to promote a thermally driven electrocyclic ring opening. Detailed mechanistic studies, supported by density functional theory (DFT) calculations, reveal a key rhodium-bound azirine intermediate that undergoes a dearomative single-carbon insertion into the biaryl framework. This reaction proceeds via a distinct, noncarbene-based pathway, expanding the scope of nitrene-mediated rearrangements beyond classical Büchner-type mechanisms. The method provides a modular route to structurally complex and photoactive scaffolds through rationally designed cascade processes.
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