Cathodic oxygen reduction-enabled rhodium-catalyzed (5 + 1) C–H/O–H annulation inspired by fuel cells

Yuan-Qiong Huang, Li Zhu and Tian-Sheng Mei ()
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Yuan-Qiong Huang: CAS
Li Zhu: CAS
Tian-Sheng Mei: CAS

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract Transition metal-catalyzed electrochemical C–H annulation with alkynes has emerged as a promising method for constructing heterocycles via formal cycloadditions. However, catalytic electrochemical C–H annulation with alkenes has been less explored. In this study, we report a cathodic oxygen reduction-enabled rhodium catalyzed (5 + 1) annulation reaction between readily available alkenylphenols and alkenes, yielding valuable 2-substituted 2H-chromenes. Unlike existing methods that involve direct oxidation of catalysts at the anode, our protocol uses a sacrificial anode to protect the substrate from overoxidation, while the cathode reduces oxygen, coupling with the RhI. to regenerate the rhodium catalyst. This efficient, atom-economical heterocyclization reaction demonstrates a broad scope and functional-group tolerance for diverse biologically relevant molecules, with a Faradaic efficiency greater than 100%.

Date: 2025
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DOI: 10.1038/s41467-025-59405-x

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