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Selective functionalization of fullerenes is an important but challenging topic in fullerene chemistry and synthetic chemistry. Here we present the first example of catalytic system-controlled regioselective 1,2- and 1,4-addition reactions for the flexible and efficient synthesis of novel 1,2- and 1,4-carbocycle-fused fullerenes via a palladium-catalyzed decarboxylative carboannulation process.
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http://dx.doi.org/10.1021/acs.orglett.4c00482 | DOI Listing |
RSC Adv
June 2025
School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences Hangzhou 310024 China
A catalytic system-controlled divergent reaction was reported to construct three distinct nitrogen-containing heterocycles from readily available starting materials a precise chemical bond activation and annulation cascade. Notably, this is the first capture of pyrazolidinones and propargyl alcohols to construct tetrahydropyrimidinones selective N-N bond activation and to generate previously unreported 3-acylindoles. This protocol demonstrates a broad substrate scope, moderate to good yields, and valuable transformations, laying a robust foundation for drug discovery applications.
View Article and Find Full Text PDFJ Org Chem
April 2025
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
Pyrazolo[1,2-]indazoles and pyrazolo[1,2-]cinnolines can be constructed selectively via catalytic system-controlled C(sp)-H activation/[4 + 1] cyclization and C(sp)-H activation/[4 + 2] cyclization reaction, utilizing pyrazolidinones and diazo indandiones. Employing two different Rh(III) catalysts, we successfully synthesized two distinct types of nitrogen-containing heterocyclic compounds, pyrazolo[1,2-]indazoles and pyrazolo[1,2-]cinnolines, respectively. Moreover, an inexpensive Ru(II) catalyst could also effectively generate pyrazolo[1,2-]cinnolines with moderate to good yields.
View Article and Find Full Text PDFOrg Lett
April 2024
Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Selective functionalization of fullerenes is an important but challenging topic in fullerene chemistry and synthetic chemistry. Here we present the first example of catalytic system-controlled regioselective 1,2- and 1,4-addition reactions for the flexible and efficient synthesis of novel 1,2- and 1,4-carbocycle-fused fullerenes via a palladium-catalyzed decarboxylative carboannulation process.
View Article and Find Full Text PDFNano Res
May 2022
Department of Laboratory Medicine, West China Hospital, Sichuan University, Chengdu, 610041 China.
The rapid spread of () causes an increased morbidity and mortality, as well as great economic losses in the world. Anti- infection becomes a major challenge for clinicians and nursing professionals to address drug resistance. Hence, it is urgent to explore high efficiency, low toxicity, and environmental-friendly methods against .
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2021
State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, Jiangsu, 210009, China.
A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N-N bond activation/[n+1] annulation cascade, a C(sp )-H activation/[4+1] annulation and a novel tandem C(sp )-H/C(sp )-H bond activation/[4+1] annulation strategy, along with a broad scope of substrates, moderate to excellent yields and valuable transformations. More importantly, in these transformations, we are the first time to capture a N-N bond activation and a C(sp )-H bond activation of pyrazolidinones under different catalytic system.
View Article and Find Full Text PDF