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

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

doi:10.1039/D2QO01114J

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

Yaxin Wang,*^ab Qin He,^a Zehui Cao,^a Peng Wang,^b Gong Chen

^c and Matthias Beller

*^b

Author affiliations

* Corresponding authors

^a College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
E-mail: 300500@njucm.edu.cn, Yaxin.Wang@catalysis.de

^b Leibniz-Institute for Catalysis, Albert-Einstein-Str. 29a, Rostock 18059, Germany
E-mail: Matthias.Beller@catalysis.de

^c State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

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.

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Article information

DOI: https://doi.org/10.1039/D2QO01114J
Article type: Research Article
Submitted: 13 Jul 2022
Accepted: 23 Aug 2022
First published: 26 Aug 2022

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Org. Chem. Front., 2022,9, 5592-5598

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

Y. Wang, Q. He, Z. Cao, P. Wang, G. Chen and M. Beller, Org. Chem. Front., 2022, 9, 5592 DOI: 10.1039/D2QO01114J

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