Visible-Light-Induced C-O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones

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Visible-light-induced intramolecular C-O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway. Detailed mechanistic studies suggest that molecular oxygen is used to trap the radical intermediate to form benzyl alcohol, which undergoes cyclization. This new approach serves as a powerful platform by providing efficient access to valuable five- and six-membered cyclic ethers and lactones with a unified protocol.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-12
Language
English
Article Type
Article
Citation

ORGANIC LETTERS, v.20, no.23, pp.7437 - 7441

ISSN
1523-7060
DOI
10.1021/acs.orglett.8b03166
URI
http://hdl.handle.net/10203/249006
Appears in Collection
CH-Journal Papers(저널논문)
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