98%
921
2 minutes
20
We report a copper-catalyzed enantioselective hydroboration of α,β-unsaturated aldehydes with pinacolborane. α,β-Unsaturated aldehydes were converted to the corresponding γ-pinacolboronate alcohols in good yields and enantioselectivities through consecutive hydroboration of the C═O and C═C bonds. This process provides simple access to the hydroborated product of allylic alcohols, and the resulting γ-pinacolboronate alcohols could be utilized in various transformations.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.8b03045 | DOI Listing |
J Am Chem Soc
September 2025
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
The carbonyl-ene reaction between aldehydes and olefins constitutes a perfectly atom economic approach to homoallylic alcohols with concomitant C-C bond formation. However, the scope of catalytic asymmetric intermolecular versions is currently limited to activated substrates, while of the two intramolecular types only catalytic asymmetric (-)-carbonyl-ene type cyclizations can be considered mature. The corresponding (-)-cyclizations would arguably find equal utility in chemical synthesis but remain underdeveloped.
View Article and Find Full Text PDFOrg Lett
September 2025
College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002, P. R. China.
A novel copper-catalyzed radical cross-coupling reaction for the thioesterification of polyfluoroarenes is developed using KS and aldehydes in water. This protocol employs a readily available KS as a sulfur source, eliminating the need for hazardous thiols and organic solvents. The mild reaction conditions are compatible with a wide range of functional groups, providing access to diverse polyfluoroaryl thioesters.
View Article and Find Full Text PDFOrg Biomol Chem
September 2025
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Despite great advances in decarbonylation of aldehydes using noble metals, the reaction is largely limited to high reaction temperatures and displays poor functional group tolerance. Herein, we report photo-irradiated decarbonylation of aldehydes, promoted by -W(N)(dppe), at room temperature. A wide range of substrates with diverse functional groups underwent decarbonylation efficiently to give the corresponding arene and alkane products in moderate to high yields.
View Article and Find Full Text PDFJ Mass Spectrom
October 2025
Department of Chemistry and Technology of Drugs, "Sapienza" University of Rome, Rome, Italy.
Ionic liquids (ILs) are a class of organic salts with melting points below 100°C. Owing to their unique chemical and physical properties, they are used as solvents and catalysts in various chemical transformations, progressively replacing common volatile organic solvents (VOCs) in green synthetic applications. However, their intrinsic ionic nature can restrict the use of mass spectrometric techniques to monitor the time progress of a reaction occurring in an IL medium, thus preventing one from following the formation of the reaction products or intercepting the reaction intermediates.
View Article and Find Full Text PDFInt J Pharm X
June 2025
Department of Respiratory and Critical Care Medicine, The First Affiliated Hospital of Wenzhou Medical University, Wenzhou 325015, China.
Ultra-sensitive pH-responsive drug delivery system designed to operate within the slightly acidic microenvironment of tumors are highly desired for hydrogel applications in cancer therapy. In this study, 4-Formylbenzoic acid modified polyvinyl alcohol (PVA-FBA, PF) was synthesized and utilized as a carrier for encapsulating the anticancer drug Doxorubicin (Dox). This was subsequently crosslinked with polyethylenimine (PEI) via benzoic-imine bond to form drug-loaded PVA-FBA/PEI hydrogel (D-PFP).
View Article and Find Full Text PDF