4.8 Article

Electrophilic C-H Borylation of Aza[5]helicenes Leading to Bowl-Shaped Quasi-[7]Circulenes with Switchable Dynamics

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Synthesis of Enantioenriched Azaborole Helicenes by Chirality Transfer from Axially Chiral Biaryls

Felix Full et al.

Summary: The enantioselective synthesis of azaborole helicenes from enantioenriched axially chiral precursors is reported. The borylation/metal-exchange reaction sequence allows for full transfer of chirality, leading to the target compounds. Experimental studies provided insights into the configurational stability and (chir)optical properties of these heterobiaryls. The structure of a phenyl-substituted helicene was confirmed by single-crystal X-ray analysis.

SYNLETT (2023)

Article Chemistry, Multidisciplinary

Metal-Free Phosphorus-Directed Borylation of C(sp2)-H Bonds

Omar Sadek et al.

Summary: A new method has been developed for the synthesis of phosphine-boranes, featuring simplicity, efficiency, and broad substrate scope. The key intermediates were identified as P-stabilized borenium cations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

BBr3-Mediated P(III)-Directed C-H Borylation of Phosphines

Jiahang Lv et al.

Summary: The study developed a metal-free P(III)-directed phosphine C-H borylation method, mediated by BBr3, to synthesize products containing both phosphorus and boron. The metal-free strategy features low cost, practicality, and environmental friendliness.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Multidisciplinary

Enhanced N-directed electrophilic C-H borylation generates BN-[5]- and [6]helicenes with improved photophysical properties

Kang Yuan et al.

Summary: This article develops an enhanced N-directed electrophilic C-H borylation methodology to access azaborine containing helicenes. The borylation process utilizes the protonation of an aminoborane with bistriflimidic acid. The synthesized helicenes show increased strain and racemization half-life, as well as improved fluorescence efficiency due to the incorporation of BN units.

CHEMICAL SCIENCE (2022)

Article Chemistry, Multidisciplinary

Enhanced Optical Properties of Azaborole Helicenes by Lateral and Helical Extension

Felix Full et al.

Summary: This article describes the synthesis and characterization of laterally extended azabora[5]-, [6]- and -[7]helicenes using N-heteroaromatic and dibenzo[g,p]chrysene building blocks. The enlargement of the pi-conjugated systems of azaborole helicenes led to compounds with improved optical properties. The combination of lateral and helical extensions resulted in a compound with a high luminescence quantum yield and dissymmetry factor, superior to its non-extended congener. The study suggests that helical and lateral extensions are viable strategies to enhance the features of azaborole helicenes.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Multidisciplinary

Phenylpyridyl-Fused Boroles: A Unique Coordination Mode and Weak B-N Coordination-Induced Dual Fluorescence

Jiang He et al.

Summary: In this study, electron-poor phenylpyridyl-fused boroles were prepared using 4-phenylpyridine or 2-phenylpyridine instead of biphenyl. The boroles exhibited unique coordination modes and different properties in solid state and solution. The enhanced electron-accepting ability of the borole species with pyridyl group was demonstrated through theoretical and experimental investigations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Metal-Free Directed C-H Borylation of Pyrroles

Zheng-Jun Wang et al.

Summary: The research presents a general strategy for site-selective C-H borylation of pyrroles using BBr3 directed by pivaloyl groups, without the need for any metal catalysts. The reaction is influenced by chelation and electronic effects, leading to diverse products with high positional selectivity and downstream transformation capabilities. DFT calculations confirm the preferred positional selectivity of this reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices

Julian Full et al.

Summary: Helically chiral compounds with one and two boron atoms were synthesized using a modular approach, showing exceptional configurational stability and fluorescence properties. The compounds are proposed as primary structures of extended helices, with potential applications in materials science.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

B,N-Embedded Double Hetero[7]helicenes with Strong Chiroptical Responses in the Visible Light Region

Ji-Kun Li et al.

Summary: This study presents unprecedented B,N-embedded double hetero[7]helicenes with excellent chiroptical properties, high absorption dissymmetry factors, and tunable circularly polarized luminescence, opening up new possibilities for the development of high-performance chiroptical materials in the future.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Construction of 1,2,3-Benzodiazaborole by Electrophilic Borylation of Azobenzene and Nucleophilic Dialkylative Cyclization

Masanori Shigeno et al.

Summary: The study presents a convenient method for the preparation of 1,2,3-benzodiazaboroles from azobenzenes, involving electrophilic ortho-borylation and dialkylative cyclization to introduce different substituents and Grignard reagents, showcasing novel reaction mechanisms and aromatic properties.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Transient Imine as a Directing Group for the Metal-Free o-C-H Borylation of Benzaldehydes

Supriya Rej et al.

Summary: Organoboron reagents play a crucial role in synthetic organic chemistry, and current selective borylation strategies rely heavily on transition-metal catalysts. However, this study introduces a transition-metal-free approach for selective C-H borylation of electron-deficient benzaldehyde derivatives, demonstrating effectiveness even in the presence of external impurities.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Bowl-Shaped Pentagon- and Heptagon-Embedded Nanographene Containing a Central Pyrrolo[3,2-b]pyrrole Core

Maciej Krzeszewski et al.

Summary: The synthesis of a bowl-shaped nitrogen-doped nanographene involves a concise strategy using multicomponent synthesis and sequential intramolecular direct arylation reactions with different reactivity of bonds, resulting in interesting properties in the final structure.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Reference Energies for Intramolecular Charge-Transfer Excitations

Pierre-Francois Loos et al.

Summary: This study provides highly accurate vertical transition energies for intramolecular charge-transfer transitions in (pi-conjugated) molecular compounds, and validates these transitions using a variety of wave functions and methods.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2021)

Review Chemistry, Multidisciplinary

Iridium-catalysed borylation of pyrene - a powerful route to novel optoelectronic materials

Yufeng Zhang et al.

Summary: The use of Ir-catalysed borylation has allowed for the effective synthesis of 2-, 4-, 2,7-, and 4,9-substituted pyrenes, as well as the investigation of their photophysics. Similar methodology has also been applied to the study of other aromatic hydrocarbons, contributing to the development of organic optoelectronics.

NEW JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Full-Color, Narrowband, and High-Efficiency Electroluminescence from Boron and Carbazole Embedded Polycyclic Heteroaromatics

Minlang Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Intramolecular (directed) electrophilic C-H borylation

S. A. Iqbal et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Multidisciplinary Sciences

Metal-free directed sp2-C-H borylation

Jiahang Lv et al.

NATURE (2019)

Article Chemistry, Multidisciplinary

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Saqib A. Iqbal et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Azabora[5]helicene Charge-Transfer Dyes Show Efficient and Spectrally Variable Circularly Polarized Luminescence

Zoe Dominguez et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Multidisciplinary

Direct regioselective C-H borylation of [5]helicene

R. P. Kaiser et al.

RSC ADVANCES (2018)

Article Chemistry, Multidisciplinary

Dimethylcethrene: A Chiroptical Diradicaloid Photoswitch

Prince Ravat et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Four-Step Synthesis of B2N2-Embedded Corannulene

Soichiro Nakatsuka et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Multidisciplinary Sciences

Chiral Buckybowl Molecules

Kuppusamy Kanagaraj et al.

SYMMETRY-BASEL (2017)

Article Chemistry, Multidisciplinary

Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency

Takashi Otani et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Organic

Selective Borylation of [4]Helicene

David Necas et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Synthesis, Structure, and Chiroptical Properties of a Double [7]Heterohelicene

Xiao-Ye Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Two-Step Synthesis of Boron-Fused Double Helicenes

Takazumi Katayama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

A boron-doped helicene as a highly soluble, benchtop-stable green emitter

Kai Schickedanz et al.

CHEMICAL COMMUNICATIONS (2015)

Review Chemistry, Multidisciplinary

New advances in nanographene chemistry

Akimitsu Narita et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism

Matthew A. Larsen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Photodissociation of B-N Lewis Adducts: A Partially Fused Trinaphthylborane with Dual Fluorescence

Kyohei Matsuo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation and Its Application in MIDA Boronate Synthesis

Viktor Bagutski et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

A Chiral Dicationic [8]Circulenoid: Photochemical Origin and Facile Thermal Conversion into a Helicene Congener

Lukas Severa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Helicenes: Synthesis and Applications

Yun Shen et al.

CHEMICAL REVIEWS (2012)

Article Chemistry, Multidisciplinary

Synthesis of 2-and 2,7-Functionalized Pyrene Derivatives: An Application of Selective C-H Borylation

Andrew G. Crawford et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Chemistry, Organic

Ir-Catalyzed Direct Borylation at the 4-Position of Pyrene

Zhiqiang Liu et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Pushing the Ir-Catalyzed C-H Polyborylation of Aromatic Compounds to Maximum Capacity by Exploiting Reversibility

Maria N. Eliseeva et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Azaboradibenzo[6]helicene: Carrier Inversion Induced by Helical Homochirality

Takuji Hatakeyama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Organic

Metal-Free Ortho C-H Borylation of 2-Phenoxypyridines under Mild Conditions

Liting Niu et al.

ORGANIC LETTERS (2012)

Article Chemistry, Multidisciplinary

The Pentaphenylborole-2,6-Lutidine Adduct: A System with Unusual Thermochromic and Photochromic Properties

Kay Ansorg et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Pinacol Boronates by Direct Arene Borylation with Borenium Cations

Alessandro Del Grosso et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Regioselectivity of the borylation of alkanes and arenes

John F. Hartwig

CHEMICAL SOCIETY REVIEWS (2011)

Article Chemistry, Multidisciplinary

Effect of the Damping Function in Dispersion Corrected Density Functional Theory

Stefan Grimme et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2011)

Review Chemistry, Multidisciplinary

C-H Activation for the Construction of C-B Bonds

Ibraheem A. I. Mkhalid et al.

CHEMICAL REVIEWS (2010)

Article Chemistry, Organic

Synthesis of Pyridine-Borane Complexes via Electrophilic Aromatic Borylation

Naoki Ishida et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

Article Chemistry, Organic

Intramolecular Cyclization of Thiophene-Based [7]Helicenes to Quasi-[8]Circulenes

Andrzej Rajca et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Physical

Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections

Jeng-Da Chai et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2008)

Article Chemistry, Physical

Accurate Coulomb-fitting basis sets for H to Rn

F Weigend

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2006)

Article Chemistry, Multidisciplinary

Ir-catalyzed borylation of C-H bonds in N-containing heterocycles: Regioselectivity in the synthesis of heteroaryl boronate esters

IAI Mkhalid et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Multidisciplinary

Structural elucidation of sumanene and generation of its benzylic anions

H Sakurai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Physical

A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP)

T Yanai et al.

CHEMICAL PHYSICS LETTERS (2004)

Review Chemistry, Inorganic & Nuclear

Transition metal-catalyzed borylation of alkanes and arenes via C-H activation

T Ishiyama et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2003)