Photocatalytic Divergent Skeletal Remodeling through Strain Release: Modular Access to Carbocycles and Heterocycles
Year: 2026
Type: preprint
Abstract: Deconstructive skeletal remodeling of three-dimensional architectures offered a unique strategy to access structurally distinct carbocyclic and heterocyclic frameworks. A common, highly strained central σ-bond enabled two divergent skeletal-reorganization pathways, providing direct access to 1,3-disubstituted naphthalenes and pyrroles. A subtle change in reaction environment dictates divergent product formation during this photocatalytic double-strain-release skeletal-remodeling process. Under rigorously anhydrous conditions, skeletal reorganization furnishes carbocycles, whereas the addition of water redirects the reaction pathway toward heterocycle formation. The method accommodates a wide range of functional groups and substitution patterns. Mechanistic studies show that both pathways proceed through a common electron-transfer manifold and shared reactive intermediate. A delicate change in reaction conditions then leads to distinct aza-diene intermediates, driving divergent, regioselective outcomes.
Source: ChemRxiv
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7221631341