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Photoredox/Cobalt-Catalyzed C(sp3)–H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution
- Source :
- Organic Letters. 22:9627-9632
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)-H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto-enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.
- Subjects :
- 010405 organic chemistry
Hydrogen bond
Organic Chemistry
chemistry.chemical_element
Phenanthrene
010402 general chemistry
Photochemistry
01 natural sciences
Biochemistry
Tautomer
Enol
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Photocatalysis
Moiety
Physical and Theoretical Chemistry
Cobalt
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 22
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi...........5059c997ef2ea7caf1bbee87f6289c66