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Rhodium-Catalyzed Homogeneous Asymmetric Hydrogenation of Naphthol Derivatives.
J Am Chem Soc
January 2025
National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, P. R. China.
Due to their strong aromaticity and difficulties in chemo-, regio-, and enantioselectivity control, asymmetric hydrogenation of naphthol derivatives to 1,2,3,4-tetrahydronaphthols has remained a long-standing challenge. Herein, we report the first example of homogeneous asymmetric hydrogenation of naphthol derivatives catalyzed by tethered rhodium-diamine catalysts, affording a wide array of optically pure 1,2,3,4-tetrahydronaphthols in high yields with excellent regio-, chemo-, and enantioselectivities (up to 98% yield and >99% ee). Mechanistic studies with experimental and computational approaches reveal that fluorinated solvent 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) plays vital roles in the control of reactivity and selectivity, and 1-naphthol is reduced via a cascade reaction pathway, including dearomative tautomerization, 1,4-hydride addition, and 1,2-hydride addition in sequence.
View Article and Find Full Text PDFVisible-Light-Induced Photocatalytic Degradation of Naproxen Using 5% Cu/TiO, Transformation Products, and Mechanistic Studies.
Molecules
December 2024
Chemistry Department, College of Science, United Arab Emirates University, Al-Ain P.O. Box 15551, United Arab Emirates.
The presence of drugs in wastewater effluent is of concern due to their effects on the aquatic fauna and flora and there are growing efforts for their removal from the environment. In this paper, we study the photocatalytic visible-light degradation of naproxen, an over-the-counter anti-inflammatory drug, using 5% copper-doped TiO. The photocatalyst was characterized by XRD and BET surface area measurements.
View Article and Find Full Text PDFProtecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1-Azido -Nucleoside.
J Org Chem
December 2024
Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
The synthesis of 1-azido -nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1-azidation with complete β-diastereoselectivity.
View Article and Find Full Text PDFInfluence of Acylation by Hydroxycinnamic Acids on the Reversible and Irreversible Processes of Anthocyanins in Acidic to Basic Aqueous Solution.
J Agric Food Chem
November 2024
LAQV - REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
In this work, the thermodynamics and kinetics of the reversible and irreversible processes of cyanidin 3,5--diglucoside and cyanidin 3--(2--glucosyl, 6--sinapoyl)glucoside-2--glucoside, 5--glucoside were studied by covering all pH range (holistic approach). The acylation (i) decreases the mole fraction of the colorless hemiketal in acidic medium and increases that of the colored quinoidal base, (ii) expands the pH domain of the flavylium cation, and (iii) moderately decreases the rate of tautomerization and isomerization of the neutral and monoanionic species. Degradation of cyanidin-3,5--diglucoside in a basic medium occurs in two distinct stages.
View Article and Find Full Text PDFPhotoexcitation Dynamics of 4-Aminopthalimide in Solution Investigated Using Femtosecond Time-Resolved Infrared Spectroscopy.
Int J Mol Sci
October 2024
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
Excited-state intramolecular proton transfer (ESIPT) reactions are crucial in photoresponsive materials and fluorescent markers. The fluorescent compound 4-aminophthalimide (4-AP) has been reported to exhibit solvent-assisted ESIPT in protic solvents, such as methanol, wherein the solvent interacts with 4-AP to form a six-membered hydrogen-bonded ring that is strengthened upon excitation. Although the controversial observation of ESIPT in 4-AP has been extensively studied, the molecular mechanism has yet to be fully explored.
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