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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Oxidation of N-Alkyl(iso)quinolinium Salts Over TEMPO@Metal-Organic Framework Heterogeneous Photocatalyst†
Shan-Shan Fu1,2, Qiang-Qiang Yuan1, Lihua Ma1,3
1MOE International Joint Laboratory of Materials Microstructure, Institute for New Energy Materials and Low Carbon Technologies, Tianjin University of Technology, Tianjin, 300384, China.
Abstract:
Quinolones and isoquinolones are of particular importance to pharmaceutical industry due to their diverse biological activities. However, their synthetic protocols were limited by high toxicity, high energy consumption, poor functional group tolerance and noble metal catalyst. This study concerns the development of a series of TEMPO@PCN-222 (TEMPO: 2,2,6,6-tetramethylpiperidinyl-1-oxy; PCN: porous coordination network) composite photocatalysts by coordinating different amount of 4-carboxy-TEMPO with the secondary building units of PCN-222. Upon visible-light irradiation, photogenerated holes in the highest occupied molecular orbital of PCN-222 can smoothly transfer to TEMPO, which can significantly boost the photosynthesis of bioactive (iso)quinolones from readily available N-alkyl(iso)quinolinium salts. TEMPO@PCN-222 exhibits an outstanding catalytic stability and substrate tolerance with a 1-methyl-2-quinolinone yield of 86.7 %, over four times that with PCN-222 (21.4 %). This work provides a new route to construct composite photocatalysts from abundant starting materials for efficient photosynthesis of high value-added chemicals.
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