期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 28, 页码 11573-11582出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001510
关键词
dearomatization; dehydrogenative; electrosynthesis; nitrogen-centered-radicals; tunablity
资金
- National Natural Science Foundation of China [21801144, 81872744, 51602164]
- Youth Innovative Talents Recruitment and Cultivation Program of Shandong Higher Education
- Natural Science Foundation of Shandong Provincie [ZR2018BB017]
- Qilu University of Technology (Shandong Academy of Sciences) [0412048811]
- Program for Scientific Research Innovation Team in Colleges and Universities of Shandong Province
Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen-centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C-N versus N-N bond formation reaction. Hence, pyrido[1,2-a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2-a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.
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