南方科技大学知识苑(SUSTech KC): Site-selective C-H difunctionalization of <i>N</i>-alkyl activated azaarenes <i>via</i> the synergistic catalysis of graphene oxide and visible light

题名	*Site-selective C-H difunctionalization of N-alkyl activated azaarenes via* the synergistic catalysis of graphene oxide and visible light**
作者	Duan, De-Hao 1; He, Hai-Ping 1; Ding, Wei-Yi3,4 ; Yi, Dong-Cheng 1; Lai, Ying-Zhen 1; Huang, Ai-Qiong 1; Liu, Jie 2; Wu, Wen-Le 2; Peng, Xiang-Jun 1
通讯作者	Peng, Xiang-Jun
发表日期	2023-09-01
DOI	10.1039/d3qo01375h
发表期刊	ORGANIC CHEMISTRY FRONTIERS 影响因子和分区
ISSN	2052-4129
卷号	10 期号:24页码:6055-6062
摘要	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.
相关链接	[来源记录]
收录类别	SCI ; EI
语种	英语
学校署名	其他
资助项目	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"]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:001079171300001
出版者	ROYAL SOC CHEMISTRY
EI入藏号	20234314928154
EI主题词	Cell death ; Drug products ; Graphene ; Lanthanum compounds ; Organocatalyst
EI分类号	Biology:461.9 ; Nanotechnology:761 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804
来源库	Web of Science
引用统计	被引频次[WOS]：1
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/582995
专题	深圳格拉布斯研究院理学院_化学系
作者单位	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
推荐引用方式 GB/T 7714	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,2023,10(24):6055-6062.
APA	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,10(24),6055-6062.
MLA	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 10.24(2023):6055-6062.