Visible-Light-Induced C–O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones
journal contributionposted on 14.11.2018, 20:18 by Honggu Im, Dahye Kang, Soyeon Choi, Sanghoon Shin, Sungwoo Hong
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.
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cyclic ethersVisible-Light-Inducedintramolecularaccesssix-membered cyclic ethersLactonetriphenylpyryliumVisible-light-inducedcyclizationregiocontrolled constructionConstructionFormationlactonepathwayabstractionTPTformationplatformBondbenzylicSix-Membered Cyclic Ethersphenyl grouptetrafluoroborateapproachform benzyl alcoholtrapsingle-electron oxidationbond