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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 25°C. 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