Tandem intramolecular electrophilic arene borylation was developed to facilitate access to B-doped polycyclic aromatic hydrocarbons (PAHs). DFT calculations revealed that electrophilic arene borylation occurred via a four-membered ring transition state, in which C-B and H-Br bonds formed in a concerted manner. An organic light-emitting diode employing the B-doped PAH as an emitter and a B-doped PAH-based field-effect transistor were successfully fabricated, demonstrating the potential of B-doped PAHs in materials science.
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http://dx.doi.org/10.1021/acs.orglett.5b03167 | DOI Listing |
Chem Commun (Camb)
January 2025
College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China.
Due to the special structure and physicochemical properties of sulfoximines, research on sulfoximines has achieved great progress in recent decades, especially in chemical and medicinal fields. This review highlights recent advancements in the N-functionalization of NH-sulfoximines, focusing on classical cross-coupling reactions with electrophilic agents and oxidative coupling reactions with extensive organic compounds, including specific (hetero)arenes, alkenes (1,4-naphthoquinones), alkanes (cyclohexanes), nucleophiles (thiols, disulfides, sulfinates, diarylphosphine oxides), organyl boronic acids, and arylhydrazines. Transition metal-catalyzed, metal-free, electrochemical and radical oxidative coupling reactions are discussed.
View Article and Find Full Text PDFBeilstein 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 PDFAngew Chem Int Ed Engl
December 2024
EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, David Brewster Road. Edinburgh, EH9 3FJ, UK.
Arene borylation reactions provide direct access to aryl organoboranes, including aryl boronic esters. Precious metals, namely Ir, Rh, Pt, remain the go-to for metal-catalysed borylation reactions, however, significant efforts have been expended in developing Earth-abundant metal alternatives. The iron-catalysed borylation of 2-aryl pyridine derivatives with 9-borabicyclo[3.
View Article and Find Full Text PDFAcc Chem Res
January 2025
State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, Tianjin 300071, China.
ConspectusElectrochemistry has been used as a tool to drive chemical reactions for more than two centuries. With the help of an electrode and a power source, chemists are provided with a system whose potential can be precisely dialed in. The theoretically infinite redox range renders electrochemistry capable of oxidizing or reducing some of the most tenacious compounds.
View Article and Find Full Text PDFJ Org Chem
December 2024
Laboratory of organic and metal-organic nitrogen-oxygen systems, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow 119991, Russian Federation.
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