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Shifting Lithium Amide Reactivity to the Radical Domain: Regioselective Radical C-H Functionalization of 3-Iodooxetane for the Synthesis of 1,5-Dioxaspiro[2.3]hexanes.
Angew Chem Int Ed Engl
January 2025
University of Bari: Universita degli Studi di Bari Aldo Moro, Dept. of Pharmacy - Drug Sciences, via E. Orabona 4, 70125, Bari, ITALY.
Strained spiro-heterocycles (SSH) have gained significant attention within the medicinal chemistry community as promising (sp3)-rich bioisosteres for their aromatic and non-spirocyclic counterparts. We herein report access to an unprecedented spiro-heterocycle - 1,5-dioxaspiro[2.3]hexane.
View Article and Find Full Text PDFFunctionalization of Pyridines at the C4 Position via Metalation and Capture.
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842-30012.
The functionalization of pyridines at positions remote to the N-atom remains an outstanding problem in organic synthesis. The inherent challenges associated with overriding the influence of the embedded N-atom within pyridines was overcome using n-butylsodium, which provided an avenue to deprotonate and functionalize the C4-position over traditionally observed addition products that are formed with organolithium bases. In this work, we show that freshly generated 4-sodiopyrdines could undergo transition metal free alkylation reactions directly with a variety of primary alkyl halides bearing diverse functional groups.
View Article and Find Full Text PDFEfficient synthesis of fluorinated triphenylenes with enhanced arene-perfluoroarene interactions in columnar mesophases.
Beilstein J Org Chem
December 2024
Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), CNRS-Université de Strasbourg (UMR 7504), F-67034 Strasbourg, France.
The high potential of non-covalent arene-fluoroarene intermolecular interactions in the design of liquid crystals lies in their ability to strongly promote self-assembly, improve the order and stability of the supramolecular mesophases, and enable tuneability of the optical and electronic properties, which can potentially be exploited for advanced applications in display technologies, photonic devices, sensors, and organic electronics. We recently successfully reported the straightforward synthesis of several mesogens containing four lateral aliphatic chains and derived from the classical triphenylene core self-assembling in columnar mesophases based on this paradigm. These mesogenic compounds were simply obtained in good yields by the nucleophilic substitution (SFAr) of various types of commercially available fluoroarenes with the electrophilic organolithium derivatives 2,2'-dilithio-4,4',5,5'-tetraalkoxy-1,1'-biphenyl (2Li- ).
View Article and Find Full Text PDFIon Hydration Enables Generality in Asymmetric Catalysis: Desymmetrization to P-Stereogenic Triarylphosphine Derivatives.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 2, Singapore, 117543, Singapore.
Asymmetric synthesis relies on seamless transmission of stereochemical information from a chiral reagent/catalyst to a prochiral substrate. The disruption by substrates' structural changes presents a hurdle in innovating generality-oriented asymmetric catalysis. Here, we report a strategy for substrate adaptability by exploiting a fundamental physicochemical phenomenon-ion hydration, in developing remote desymmetrization to access P-stereogenic triarylphosphine oxides and sulfides.
View Article and Find Full Text PDFNickel-Catalyzed Difluoroalkylation of β,γ-Unsaturated α-Amino Nitrile Derived Lithium Reagents.
Angew Chem Int Ed Engl
November 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032, Shanghai, China.
Organolithium reagents, known for their low cost, ready availability, and high reactivity, allow fast cross-coupling under ambient conditions. However, their direct cross-coupling with fluoroalkyl electrophiles remains a formidable challenge due to the easy formation of thermo-unstable fluoroalkyl lithium species during the reaction, which are prone to decomposition via rapid α/β-fluoride elimination. Here, we exploit heteroatom-stabilized allylic anions to harness the exceptional reactivity of organolithium reagents, enabling the compatibility of difluoroalkyl halides and facilitating versatile and precise fluorine functionality introduction under mild conditions.
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