Journal
ORGANIC LETTERS
Volume 22, Issue 24, Pages 9627-9632Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03665
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Funding
- National Natural Science Foundation of China [22088102, 21933007, 21861132004]
- Ministry of Science and Technology of China [2017YFA0206903]
- Strategic Priority Research Program of the Chinese Academy of Science [XDB17000000]
- Key Research Program of Frontier Sciences of the Chinese Academy of Science [QYZDY-SSW-JSC029]
- K. C. Wong Education Foundation
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The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp(3))-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.
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