Visible-Light-Enabled Lanthanum-Mediated Intramolecular Epoxy-Ring Opening/Dehydrogenative Lactonization

Catalytic C­(sp3)–H functionalization has afforded great opportunities to prepare organic substances, facilitating the derivatization of complex drugs and natural molecules. This letter describes an efficient and practical protocol for lanthanum-catalyzed continuous epoxy-ring opening and oxidative...

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Published inOrganic letters Vol. 25; no. 39; pp. 7126 - 7131
Main Authors Cai, Lina, Lai, Qihong, Zhang, Lele, Xue, Guotao, Zhang, Yirui, He, Na, Huang, Mingqiang, Hu, Shirong, Cai, Shunyou
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.10.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
ACTIVATION
ALKYNES
ALKYLATION
C-H BONDS
PHOTOCATALYSIS
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Summary:Catalytic C­(sp3)–H functionalization has afforded great opportunities to prepare organic substances, facilitating the derivatization of complex drugs and natural molecules. This letter describes an efficient and practical protocol for lanthanum-catalyzed continuous epoxy-ring opening and oxidative dehydrogenative lactonization under visible-light irradiation. Notably, the lanthanum catalyst also acts as a photocatalyst while acting as a Lewis acid in this reaction; therefore, no additional photocatalyst is required. We can conveniently prepare a series of diverse isochromanones with oxygen-containing spirocyclic structural units under a balloon-oxygen atmosphere at room temperature. Mechanistic studies and control experiments reveal that the in situ-generated lanthanum bromide should be crucial in the reaction.
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c02589