Direct Excitation of Aldehyde to Activate the C(sp2)−H Bond by Cobaloxime Catalysis toward Fluorenones Synthesis with Hydrogen Evolution
Dr. Jia-Dong Guo
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorYa-Jing Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorChen-Hong Wang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorQiao He
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorDr. Xiu-Long Yang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorTian-Yu Ding
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorKe Zhang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorRui-Nan Ci
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorDr. Bin Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorProf. Dr. Chen-Ho Tung
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Li-Zhu Wu
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorDr. Jia-Dong Guo
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorYa-Jing Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorChen-Hong Wang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorQiao He
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorDr. Xiu-Long Yang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorTian-Yu Ding
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorKe Zhang
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorRui-Nan Ci
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorDr. Bin Chen
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorProf. Dr. Chen-Ho Tung
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Li-Zhu Wu
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing, 100190 P. R. China
School of Future Technology, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China
Search for more papers by this authorAbstract
A new way to form fluorenones via the direct excitation of substrates instead of photocatalyst to activate the C(sp2)−H bond under redox-neutral condition is reported. Our design relies on the photoexcited aromatic aldehyde intermediates that can be intercepted by cobaloxime catalyst through single electron transfer for following β-H elimination. The generation of acyl radical and successful interception by a metal catalyst cobaloxime avoid the use of a photocatalyst and stoichiometric external oxidants, affording a series of highly substituted fluorenones, including six-membered ketones, such as xanthone and thioxanthone derivatives in good to excellent yields, and with hydrogen as the only byproduct. This catalytic system features a readily available metal catalyst, mild reaction conditions and broad substrate scope, in which sunlight reaction and scale-up experiments by continuous-flow approach make the new methodology sustainable and amenable for potentially operational procedures.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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