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This paper reports a room temperature visible-light-driven protocol for the intermolecular [2+2] cycloadditions between coumarin-3-carboxylates and acrylamides analogs by an energy-transfer process. Using an iridium complex FIrPic as a photosensitizer and a 3 W blue LED as a light source, an array of cyclobutabenzocypyranones were prepared in moderate to excellent yields.
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http://dx.doi.org/10.1002/chem.201501176 | DOI Listing |
Beilstein J Org Chem
September 2025
Chemistry and Materials Program, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
In single crystals of C-N atropisomeric -(2-halophenyl)quinolin-2-one and the thione analogue, a unique association based on a halogen-π interaction was detected. In racemic and optically pure -(2-bromo- or 2-chlorophenyl)quinolin-2-ones, homochiral layered polymers, which consist of ()- or ()-atropisomers, were formed through intermolecular halogen-π association. The halogen-π association in the racemates is due to a halogen bond (C-X···π) between a σ-hole on the halogen atom and a π-electron on the quinolinone benzene ring, while that in optically pure forms is caused by an n-π* interaction between a lone electron pair on the halogen atom and a π* orbital of the quinolinone.
View Article and Find Full Text PDFChem Sci
August 2025
Department of Chemistry, Indian Institute of Technology Bombay Powai Mumbai - 400076 India
The supramolecular organization of functional molecules at the mesoscopic level influences their material properties. Typically, planar π-conjugated (disc- or linear-shaped) molecules tend to undergo one-dimensional (1D) stacking, whereas two-dimensional (2D) organization from such building blocks is seldom observed in spite of their technological potential. Herein, we rationally achieve both 1D and 2D organizations from a single planar, π-conjugated molecular system competitive interactions.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Pune-410008, India.
A facile and efficient one-pot rongalite-mediated self-dimerization of 3-acylidene-2-oxindoles has been developed for the diastereoselective synthesis of highly functionalized dispirocyclopentanebisoxindoles. The reaction proceeds a domino sequence involving intermolecular Michael addition followed by intramolecular aldol cyclization under basic conditions. Rongalite, an inexpensive and readily available reagent (∼$0.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080-3021, United States.
The direct transformation of C-H bonds into C-C bonds via cross-dehydrogenative coupling (CDC) represents a powerful strategy in synthetic chemistry, enabling streamlined bond construction without the need for prefunctionalized substrates. While traditional CDC approaches rely on polar mechanisms and preactivation of one of the C-H partners, recent advances have introduced radical-based strategies that employ a hydrogen atom transfer (HAT) approach to access carbon-centered radicals from unactivated substrates. Herein, we report a nickel-catalyzed CDC reaction between aldehydes and alkenes for the synthesis of skipped enones, leveraging aryl radicals as intermolecular HAT agents.
View Article and Find Full Text PDFInt J Biol Macromol
September 2025
University of Ljubljana, Faculty of Pharmacy, Aškerčeva 7, 1000, Ljubljana, Slovenia. Electronic address:
Monoclonal antibodies (mAb) have transformed modern medicine, offering targeted therapies for cancer, autoimmune disorders, and infectious diseases. To enhance patient convenience, subcutaneous administration is increasingly prioritized, requiring highly concentrated formulations. However, high viscosity of these formulations hinders manufacturability, injectability, and stability.
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