Hypervalent-iodine promoted selective cleavage of C(sp3)-C(sp3) bonds in ethers

Yaxin Wang, Qin He, Zehui Cao, Yaxin Wang, Peng Wang, Matthias Beller, Gong Chen

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A visible-light-promoted and radical-mediated strategy for the site-specific cleavage of C(sp3)-C(sp3) bonds in ethers is reported. Different cyclic and linear alkyl ethers are converted into benzoylated acetals and aldehydes or ketones under mild conditions in the presence of Ru(bpy)3Cl2 as a photocatalyst and Zhdankin's λ3-azidoiodane reagent in moderate to high yields. Control experiments and mechanistic investigations provide a plausible mechanism for this unusual deconstructive esterification of ethers.

Original languageEnglish
Pages (from-to)5592-5598
Number of pages7
JournalOrganic Chemistry Frontiers
Volume9
Issue number20
DOIs
StatePublished - 26 Aug 2022
Externally publishedYes

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