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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.5b03167DOI Listing

Publication Analysis

Top Keywords

electrophilic arene
12
arene borylation
12
polycyclic aromatic
8
aromatic hydrocarbons
8
tandem intramolecular
8
intramolecular electrophilic
8
synthesis boron-doped
4
boron-doped polycyclic
4
hydrocarbons tandem
4
borylation tandem
4

Similar Publications

Advances in cross-coupling and oxidative coupling reactions of NH-sulfoximines - a review.

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 PDF

Efficient 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 PDF

Multifaceted Hidden Catalysis Revealed by Mechanistic Analysis of FeBr-Catalysed Arene Borylation.

Angew 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 PDF

Electroreductive Cross-Coupling Reactions: Carboxylation, Deuteration, and Alkylation.

Acc 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 PDF

Electrophilic Intermediates in the Nef and Meyer Reactions: A Computational Study.

J 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.

Article Synopsis
  • The study used quantum-chemical calculations to explore how nitroalkanes activate when combined with protic acids, focusing on the Nef and Meyer reactions.
  • It identified that specific cationic species, including -bis(hydroxy)iminium and -oxoiminium, form independently from nitroalkanes, and -hydroxynitrilium cations result from C-H bond cleavage in -oxoiminium.
  • The findings suggest these cations are strong electrophiles that can react with nonactivated arenes under normal conditions, offering insights into the mechanisms of the Nef and Meyer reactions and hinting at possible new reaction pathways.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!