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 in | Organic letters Vol. 25; no. 39; pp. 7126 - 7131 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
06.10.2023
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. 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.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. Catalytic C(sp(3))-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. |
| Author | Zhang, Yirui He, Na Lai, Qihong Zhang, Lele Huang, Mingqiang Cai, Lina Xue, Guotao Cai, Shunyou Hu, Shirong |
| AuthorAffiliation | Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry, Chemical Engineering, and Environment Key Laboratory of Chemical Genomics of Guangdong Province, School of Chemical Biology and Biotechnology, Shenzhen Graduate School |
| AuthorAffiliation_xml | – name: Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry, Chemical Engineering, and Environment – name: Key Laboratory of Chemical Genomics of Guangdong Province, School of Chemical Biology and Biotechnology, Shenzhen Graduate School |
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| Keywords | CATALYSIS ACTIVATION ALKYNES ALKYLATION C-H BONDS PHOTOCATALYSIS |
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| Snippet | Catalytic C(sp3)–H functionalization has afforded great opportunities to prepare organic substances, facilitating the derivatization of complex drugs and... Catalytic C(sp(3))-H functionalization has afforded great opportunities to prepare organic substances, facilitating the derivatization of complex drugs and... Catalytic C(sp3)-H functionalization has afforded great opportunities to prepare organic substances, facilitating the derivatization of complex drugs and... |
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| Title | Visible-Light-Enabled Lanthanum-Mediated Intramolecular Epoxy-Ring Opening/Dehydrogenative Lactonization |
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