Site-selective C-H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light

Duan, De-Hao1; He, Hai-Ping1; Ding, Wei-Yi3,4; Yi, Dong-Cheng1; Lai, Ying-Zhen1; Huang, Ai-Qiong1; Liu, Jie2; Wu, Wen-Le2; Peng, Xiang-Jun1

2023-09-01

10.1039/d3qo01375h

ORGANIC CHEMISTRY FRONTIERS   Impact Factor & Quartile

2052-4129

Strategies for site-selective C-H difunctionalization on N-alkyl activated azaarenes have attracted considerable attention as a powerful tool in heterocyclic chemistry. By employing graphene oxide (GO) as a heterogeneous cocatalyst, the visible light-induced site-selective difunctionalizations of pyridiniums/quinoliniums provided a distinct and straightforward synthetic route toward C4- and C2-selective phosphonation of the pyridinone/quinolinone/quinolone cores. Furthermore, the site-selectivity on quinoliniums could be successfully switched from C4 to C2 by changing the base and solvent. This coordination of catalysis systems drove the regioselective phosphonyl radical and phosphoryl anion addition to N-alkyl activated azaarenes, respectively, and subsequent oxidation with air as the terminal oxidant. In vitro antitumor studies showed that complex 3c participated in mitochondria-mediated pathways on the apoptosis of HeLa cells to 42.2% (21 mu M). Phosphorus-based organocatalyst 4e, as one of the optical materials, offered efficient tuning of the emission and quantum yields.

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The authors are grateful to the National Natural Science Foundation of China (22261004), the Fundamental Research Funds for Gannan Medical University (QD202023), the Horizontal Cooperation Project (HX202201), and Innovation Project for Postgraduate Innovat[22261004] ; National Natural Science Foundation of China[QD202023] ; Fundamental Research Funds for Gannan Medical University[HX202201] ; Horizontal Cooperation Project["S202210413018","BKSZR39"]

Chemistry

Chemistry, Organic

WOS:001079171300001

ROYAL SOC CHEMISTRY

Web of Science

1.Gannan Med Univ, Sch Pharmaceut Sci, Key Lab Prevent & Treatment Cardiovasc & Cerebrova, Minist Educ, Ganzhou 341000, Peoples R China
2.Gannan Med Univ, Sch Med Informat Engn, Ganzhou 341000, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China

Duan, De-Hao,He, Hai-Ping,Ding, Wei-Yi,et al. Site-selective C-H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light[J]. ORGANIC CHEMISTRY FRONTIERS,2023.

Duan, De-Hao.,He, Hai-Ping.,Ding, Wei-Yi.,Yi, Dong-Cheng.,Lai, Ying-Zhen.,...&Peng, Xiang-Jun.(2023).Site-selective C-H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light.ORGANIC CHEMISTRY FRONTIERS.

Duan, De-Hao,et al."Site-selective C-H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light".ORGANIC CHEMISTRY FRONTIERS (2023).