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Silver(I)-Catalyzed Reductive Cross-Coupling of Aldehydes to Structurally Diverse Cyclic and Acyclic Ethers

Ting Liang, Guichao Dong, Chuang Li, Xin Xu and Zhou Xu*

*Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, Tongshan Road 209, Xuzhou 221004, China, Email: xuzhouxzhmu.edu.cn

T. Liang, G. Dong, C. Li, X. Xu, Z. Xu, Org. Lett., 2022, 24, 1817-1821.

DOI: 10.1021/acs.orglett.2c00270


Abstract

Medium-sized cyclic ethers have been effectively synthesized through intramolecular reductive coupling of dialdehydes in the presence of a hydrosilane and low loadings of AgNTf2 as catalyst at 25C. The catalytic system is also suitable for the coupling of two different monoaldehydes to provide unsymmetrical ethers. This protocol features broad functional group compatibility and high product diversity.

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proposed mechanism



Key Words

cyclic ethers, reductive etherification, triethylsilane


ID: J54-Y2022