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Heterogeneous Copper Single-Atom Catalyzed Three-Component Radical Difunctionalization of Alkenes
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J
K
J
DOI：10.1002/adsc.70257.png)
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Abstract
En 中文
Multicomponent alkene difunctionalization is persistently challenged by the difficult recovery of homogeneous catalysts and limited applicability to unactivated alkenes. While single-atom catalysts (SACs) hold promise for overcoming these limitations, their application to such complex transformations remains unexplored thus far. Herein, we developed a Cu SAC (Cu1@NC) featuring atomically dispersed Cu–N4 sites that enable efficient three-component coupling of alkenes, quinoxalinones, and polyhalogenated alkanes. This catalytic system simultaneously installs both gem-dihaloalkyl and quinoxalinone pharmacophores across a broad substrate scope (52 examples), including traditionally challenging unactivated aliphatic alkenes. Remarkably, Cu1@NC maintains excellent catalytic stability over >10 cycles with >95% of its initial activity retained and demonstrates robust scalability (72%–77% isolated yields in gram-scale reactions). Most significantly, this catalytic system enables efficient late-stage difunctionalization of alkenes derived from complex bioactive molecules (e.g., ibuprofen, borneol derivatives), underscoring its potential for pharmaceutical applications. Mechanistic investigations reveal that Cu1@NC mediates the radical pathway through two essential single-electron transfer processes: activating TBHP to generate oxygen-centered radicals and oxidizing intermediate IM-4 to regenerate the catalytic center. This study delivers an atom- and step-economical route to valuable drug-like scaffolds, thus opening new avenues for heterogeneous catalysis in multicomponent reactions.
Keywords:
alkenes
copper single-atom catalysis
heterogeneous catalysis
quinoxalinones
three-component difunctionalization
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2.6W
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