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Lewis Acid-Mediated Regioselective Hydrofunctionalization of Styrenes with Isatins and Heterocycles.
J Org Chem
January 2025
School of Chemistry, IGCME, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
The ligand-free Lewis acid-mediated regioselective hydroamination and hydroarylation of styrenes have been successfully developed in the presence of isatins or heterocyclic aryl compounds such as benzothiophenes and benzofurans. The reactions tolerate a variety of functional groups and afford the corresponding products in moderate to good yields. Deuterium labeling experiments show that the functionalized hydrogen of styrenes was derived from the nitrogen-hydrogen of the substrates in the hydroamination.
View Article and Find Full Text PDFAccessing Azetidines through Magnesium-Mediated Nitrogen Group Transfer from Iminoiodinane to Donor-Acceptor Cyclopropanes.
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, New York University, New York, New York, 10003, United States.
Herein, we report a Lewis acid-mediated ring expansion of donor-acceptor cyclopropanes (DACs) to substituted azetidines via nucleophilic nitrogen group transfer from readily accessible iminoiodinane. This protocol operates under mild, transition-metal-free conditions, and showcases excellent chemoselectivity, along with broad functional group tolerance. We report for the first time that challenging alkyl donor-acceptor cyclopropanes can undergo ring expansion leading to aliphatic azetidines without relying on external oxidants or precious transition-metal catalysts.
View Article and Find Full Text PDFBF-Mediated C2-Amidation of Quinoline Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-(Trifluoroethyl)amidoquinolines.
Org Lett
January 2025
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
A Lewis acid-mediated C2-trifluoroethylamidation of quinolines, employing quinoline oxides, trifluorodiazoethane, and acetonitrile to forge a new class of (quinolin2-yl)-(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-(trifluoroethyl)acetamide derivatives in high yields.
View Article and Find Full Text PDFLewis Acid-Mediated Interfacial Water Supply for Sustainable Proton Exchange Membrane Water Electrolysis.
J Am Chem Soc
December 2024
College of Materials Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 210016, China.
The catalyst-electrolyte interface plays a crucial role in proton exchange membrane water electrolysis (PEMWE). However, optimizing the interfacial hydrogen bonding to enhance both catalytic activity and stability remains a significant challenge. Here, a novel catalyst design strategy is proposed based on the hard-soft acid-base principle, employing hard Lewis acids (LAs = ZrO, TiO, HfO) to mediate the reconfiguration of interfacial hydrogen bonding, thereby enhancing the acidic oxygen evolution reaction (OER) performance of RuO.
View Article and Find Full Text PDFPhotoredox Activation of Donor-Acceptor Cyclopropanes: Distonic Radical Cation Reactivity in [3+2] Cycloaddition Reactions.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Jharkhand, 826004, India.
Article Synopsis
- Altering the reactivity of molecules could resolve current limitations, especially for Donor-Acceptor Cyclopropanes (DACs) which have relied on Lewis acids for activation.
- Unpolarized alkenes present challenges due to a polarity mismatch with the Lewis acid-mediated zwitterionic intermediate, hindering their coupling.
- Using photoredox catalysis to leverage the distonic radical cation approach successfully navigates this mismatch, allowing for the formation of highly substituted cyclopentanes and facilitating new pathways to create bicyclo[3.1.1]heptanes through a unique [3σ+2σ] cycloaddition process.
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