Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 20, Pages 5592-5598Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01114j
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Funding
- National Natural Science Foundation of China [22001128]
- National Science Foundation of Jiangsu Province [BK20200847]
- National Science Foundation of Nanjing University of Chinese Medicine [NZY22001128]
- CSC scholarship
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This study reports a visible-light-promoted and radical-mediated strategy for the site-specific cleavage of C(sp(3))-C(sp(3)) bonds in ethers. Different cyclic and linear alkyl ethers can be converted into benzoylated acetals and aldehydes or ketones under mild conditions in the presence of Ru(bpy)(3)Cl-2 as a photocatalyst and Zhdankin's lambda(3)-azidoiodane reagent, with moderate to high yields. Control experiments and mechanistic investigations provide a plausible mechanism for this unusual deconstructive esterification of ethers.
A visible-light-promoted and radical-mediated strategy for the site-specific cleavage of C(sp(3))-C(sp(3)) 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)(3)Cl-2 as a photocatalyst and Zhdankin's lambda(3)-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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