Palladium-catalyzed dual C-H functionalization of benzophenones to form fluorenones by oxidative dehydrogenative cyclization is reported. This method provides a concise and effective route toward the synthesis of fluorenone derivatives, which shows outstanding functional group compatibility.
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http://dx.doi.org/10.1021/ol302181z | DOI Listing |
J Org Chem
January 2025
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. China.
An efficient method for construction of various fluorenones has been achieved via Rh(III)-catalyzed C-H activation/[4 + 2] annulation/aromatization sequences of simple and readily available enaminones and 1,3-dienes. This protocol showed good substrate compatibility as an array of structurally and electronically diverse fluorenones prepared efficiently in moderate to good yields and preparative scale utility showing very good efficiency in the late-stage functionalization of complex valuable molecules.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350116, China.
This study describes the synthesis and potential applications of pentaaryl-substituted pyrroles. We report a Pd-catalyzed approach for their preparation from 4,5-diyne-9-fluorenone (1,7-diyne) and aromatic amines. The target nitrogen-doped corannulenes () were investigated computationally to understand their electronic properties.
View Article and Find Full Text PDFSci Rep
November 2024
Department of Biotechnology, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran.
This study provides thorough computational and experimental assessments of four types of novel synthesized thiosemicarbazones. The compounds were effectively synthesized using a condensation reaction between thiosemicarbazide and fluorenone, producing a remarkable range of 70-88%. Additional chemical structures were examined utilizing spectroscopic methods, including Fourier-transform infrared spectroscopy (FTIR), NMR spectroscopy, and ultraviolet-visible spectroscopy.
View Article and Find Full Text PDFJ Med Chem
November 2024
Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
Inhibition of the protein-protein interaction between Kelch-like ECH-associated protein 1 (Keap1) and nuclear factor erythroid 2-related factor 2 (Nrf2) has been recognized as an attractive approach for treating oxidative stress-related diseases. Here, we present a new series of noncovalent Keap1-Nrf2 inhibitors developed by a conformational restriction strategy of our fluorenone-based compounds previously identified by fragment-based drug discovery. The design was guided by X-ray cocrystal structures, and the subsequent optimization process aimed at improving affinity, cellular activity, and metabolic stability.
View Article and Find Full Text PDFChem Sci
October 2024
KAUST Catalysis Center, KCC, King Abdullah University of Science and Technology, KAUST Thuwal 23955-6900 Saudi Arabia
Photocatalytic molecular oxygen activation has emerged as a valuable tool for organic synthesis, environmental remediation and energy conversion. Most reported instances have relied on high-energy light sources. Herein, 9-fluorenone-functionalized porous organic polymers (POPs) were reported to enable red-light-excited photocatalysis for the organic oxygenation reaction.
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