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Updated: Jul 22, 2025

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Methylene-Bridged Dimerization by Cu-Catalyzed Deconstructive C-C Cleavage of Oxacycloalkane
Xu Yuan1, Jimei Yang1, Xingjiang Yang1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, P. R. China.
Abstract:
Herein, we demonstrate the successful utilization of copper catalysis and oxygen oxidation for consecutive C(sp3)-C(sp3) bond cleavage in alkyl cyclic ethers. A key step involves a copper-oxygen autoxidation process, generating in situ alkoxy radicals and triggering sequential C-C bond cleavage. This β-oxidative cleavage strategy enables the use of cyclic ethers as valuable C1 building blocks for the synthesis of bridged methylene dimers. This reaction holds promise for inspiring alternative methods targeting inert C(sp3)-C(sp3) bond cleavage.
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