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Reported herein, for the first time, is a copper-promoted intramolecular [4+2]-cycloaddition cascade to access ionic N-doped polycyclic aromatic hydrocarbons (PAHs) with tunable emission wavelengths. It is shown that the reaction can be made catalytic with respect to Cu(OTf)2 when an external oxidant, Selectfluor, was used.
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http://dx.doi.org/10.1039/c8cc05743e | DOI Listing |
Inorg Chem
September 2025
Department of Chemistry, Panskura Banamali College, Panskura RS, Purba Medinipur, WB 721152, India.
We report the synthesis and characterization of a new Schiff base ligand (HL), derived from 2-picolylamine and 2-hydroxy-3-methoxy-5-methylbenzaldehyde. Its reaction with Ni(NO)·6HO and Ln(NO)·HO (Ln = Gd, Tb, Dy) in the presence of triethylamine affords a carbonato-bridged family of heterobimetallic NiLn complexes: [NiLn(L)(L')(μ-CO)(NO)]·MeOH·HO (). During the complexation reaction, ligand HL undergoes an oxidation, followed by C-C coupling to generate a secondary ligand (HL').
View Article and Find Full Text PDFChem Commun (Camb)
September 2025
Department of Chemistry, College of Pharmacy, North China University of Science and Technology, Tang Shan, P. R. China.
Singlet oxygen (O) plays a crucial role in cancer chemotherapy and ROS biology, driving the need for highly specific probes to monitor its dynamics in real time. Herein, we developed the ratiometric fluorescent probe NAP-t-PY, utilizing a 2-pyridone recognition unit. The probe's 1-methyl-3-benzyl-2-pyridone moiety reacts specifically with O [4 + 2] cycloaddition, forming the endoperoxide NAP-t-PY-EP.
View Article and Find Full Text PDFOrg Lett
September 2025
School of Pharmacy and Food Engineering, Wuyi University, Jiangmen 529090, P. R. China.
3-Fluoropyrroles are privileged scaffolds in pharmaceutical and agrochemical applications, yet their synthesis remains challenging. Herein, we report a palladium(0)-catalyzed [4+1] cycloaddition/dehydration strategy for the efficient construction of 3-fluoropyrroles from readily available 3,3-difluoropent-4-en-2-ones and primary amines. This transformation proceeds via C-F bond activation to generate a key π-allyl-Pd(II) intermediate, followed by intramolecular addition/dehydration to furnish the heterocyclic core.
View Article and Find Full Text PDFTetrahedron
June 2025
Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Nashville, Tennessee 37235, United States.
Yaretol is a polycyclic norditerpene constituting a structurally distinct class of terpene natural products isolated from which, to date, has not been accessed via total synthesis. Herein, we report our synthetic efforts toward a key intramolecular Diels-Alder furan (IMDAF) cycloaddition to construct the carbon framework. We discuss our efforts toward the cycloaddition wherein undesired aromatization and unanticipated rearrangement of the cycloadduct are observed.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya 464-8601, Japan.
A new synthesis route to 2,6-diazabicyclo[3.3.1]nonanes as a scaffold of conformationally restricted diamines is disclosed.
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