Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Chemical Reviews, Journal Year: 2020, Volume and Issue: 121(14), P. 9113 - 9163

Published: Dec. 14, 2020

Often stoichiometric amounts of gold find use in materials science; occasionally is even used as a support. This review discusses the contributions catalysis, both homogeneous and heterogeneous, to field science. One topic synthesis polymers, including nanowires polyesters, postcyclization polymerization by cyclopropanation, gold-catalyzed radical reactions. Other topics are dyes, phosphonium salts, wide range extended conjugated π-systems, latter ranging from acenes, pentalene derivatives, different heterocyclic π-systems fascinating applications helical anellated aromatic molecules. The existing clearly demonstrate potential catalysis for significant future impulses

Language: Английский

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Gold‐Catalyzed Regiospecific C−H Annulation of o‐Ethynylbiaryls with Anthranils: π‐Extension by Ring‐Expansion En Route to N‐Doped PAHs

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(23), P. 6935 - 6939

Published: April 10, 2018

Abstract We describe a novel, short, and flexible approach to diverse N‐doped polycyclic aromatic hydrocarbons (PAHs) through gold‐catalyzed π‐extension of anthranils with o ‐ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due high step atom economy, shows good functional‐group compatibility well scale‐up potential. Mechanistically, the tandem reaction proposed involve nucleophilic addition/ring opening/regiospecific C−H annulation/protodeauration sequence terminated by Friedel–Crafts‐type cyclization. Photophysical studies products indicated violet‐blue fluorescence emission quantum yields up 0.45.

Language: Английский

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Recent Advances in C–H Activation for the Synthesis of π-Extended Materials

ACS Materials Letters, Journal Year: 2020, Volume and Issue: 2(8), P. 951 - 974

Published: June 29, 2020

The activation of typically unreactive aromatic C–H bonds by transition-metal catalysis has been receiving increased attention from the synthetic chemistry community in recent years. Advances this area have enabled direct and site-selective modification rings without need for pre-functionalization. Accordingly, these techniques found broad application many fields, including construction extended π-systems use materials science. This review will discuss reports reactions applied toward synthesis π-extended functional materials.

Language: Английский

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Transition Metal‐Catalyzed Intermolecular Cascade C−H Activation/Annulation Processes for the Synthesis of Polycycles

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(1), P. 121 - 144

Published: June 12, 2020

Abstract Polycycles are abundantly present in numerous advanced chemicals, functional materials, bioactive molecules and natural products. However, the strategies for synthesis of polycycles limited to classical reactions transition metal‐catalyzed cross‐coupling reactions, requiring pre‐functionalized starting materials lengthy synthetic operations. The emergence novel approaches shows great promise fields organic/medicinal/materials chemistry. Among them, C−H activation followed by intermolecular annulation prevail, due their straightforward manner with high atom‐ step‐economy, providing rapid, concise efficient methods construction diverse polycycles. Several have been developed polycycles, relying on sequential multiple activation/annulation, or combination activation/annulation further interaction a proximal group, merger cycloaddition reaction, situ formation directing group. These attractive, efficient, step‐ atom‐economic from commercially available materials. This Minireview will provide an introduction helping researchers discover indirect connections reveal hidden opportunities. It also promote discovery activation.

Language: Английский

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In Situ Generation of Azonia-Containing Polyelectrolytes for Luminescent Photopatterning and Superbug Killing

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(28), P. 11259 - 11268

Published: June 20, 2019

Polyelectrolytes play an important role in both natural biological systems and human society, their synthesis, functional exploration, profound application are thus essential for biomimicry creating new materials. In this study, we developed efficient synthetic methodology situ generation of azonia-containing polyelectrolytes a one-pot manner by using readily accessible nonionic reactant the presence commercially available cheap ionic species. The resulting emissive solid state can form luminescent photopatterns with different colors. possess extraordinary potency reactive oxygen species (ROS) generation, enabling them to impressively kill methicillin-resistant Staphylococcus aureus (MRSA), drug resistant superbug, vitro vivo.

Language: Английский

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Multiple annulations of inert C(sp²)–H bonds with alkynes

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(29), P. 4561 - 4587

Published: Jan. 1, 2022

This feature article uncovers a tactical blueprint for the sustainable development of synthetic manifestations in transition-metal catalyzed directing group assisted multiple annulations (L-type, Y-type, and B-type) inert C(arene)–H bonds.

Language: Английский

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Transition-Metal-Catalyzed C–C Bond-Forming Reactions via C–H Activation for the Development of Fluorescent Materials with Practical Value

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 2796 - 2820

Published: Feb. 14, 2022

Fluorescent materials of practical value have attracted considerable attention because their important applications in the fields bioprobes, chemosensors, organic light-emitting diodes, field-effect transistors, memory devices, security systems, etc. As such, these been improving quality our daily life. In past few decades, chemists and scientists constructed various fluorescent molecules using transition-metal-catalyzed C–C bond-forming reactions via C–H activation. This approach provides a unique opportunity for efficient straightforward access to frameworks that cannot be easily by traditional synthetic routes. Review aims highlight help better understand recent development activation optimized value. addition, some perspectives on challenges opportunities this field will discussed.

Language: Английский

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Palladium‐Catalyzed para‐Selective Alkylation of Electron‐Deficient Arenes

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(21), P. 6294 - 6298

Published: April 12, 2018

Abstract Intermolecular alkylations of electron‐deficient arenes proceed with good para selectivity. Palladium catalysts were used to generate nucleophilic alkyl radicals from halides, which then directly add onto the arenes. The arene scope and site alkylation are opposite those classical Friedel–Crafts alkylations, prefer electron‐rich systems.

Language: Английский

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Copper-Catalyzed C4-H Regioselective Phosphorylation/Trifluoromethylation of Free 1-Naphthylamines

Organic Letters, Journal Year: 2019, Volume and Issue: 21(2), P. 486 - 489

Published: Jan. 2, 2019

A novel and facile copper-catalyzed synthetic methodology was developed to access a large variety of 4-phosphoryl-substituted 1-naphthylamines by reacting various with different diarylphosphine oxides in the presence Cu(OAc)2 Ag2CO3 one pot under mild reaction conditions. This system also suitable for being employed synthesize 4-trifluoromethyl-substituted Togni's reagent CuI NaOAc DMSO

Language: Английский

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Cu(I)-Catalyzed 6-endo-dig Cyclization of Terminal Alkynes, 2-Bromoaryl Ketones, and Amides toward 1-Naphthylamines: Applications and Photophysical Properties

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(6), P. 2535 - 2544

Published: Jan. 23, 2019

Functional group substituted 1-naphthylamines, especially N-methylated ones, play important roles in numerous chemical and biological processes. However, these compounds' general step-economic syntheses are highly limited, which seriously restricts efforts to improve the properties develop new functions for this kind of compound. In report, we describe development an efficient, convenient, method synthesis valuable functionalized 1-naphthylamines directly from readily available terminal alkynes, 2-bromoaryl ketones, amides via Cu(I)-catalyzed benzannulation a green solvent (i.e., water) under Pd- ligand-free conditions. A total 82 synthetically biologically useful compounds, synthesized isolated yields up 95%. Some unique features reaction as follows: (1) exclusive 6-endo-dig selectivity, (2) ready incorporation broad range functional groups easily substrates, (3) that can be used aminating agents excellent alternatives toxic and/or odorous amines. Due facile tuning reaction, products possess good electronic donor–acceptor structures exhibit intriguing photophysical properties, such tunable polarity-sensitive fluorescence emission large Stokes shifts (up 258 nm). Utilizing products' response, successfully applied 1-naphthylamine derivatives, compound 91, image lipid droplets (LDs) monitor cellular LDs growth. The previously mentioned advantages methodology, along with mild conditions, simple operation, scalable synthesis, may allow novel extended varied applications chemistry, biology, materials science.

Language: Английский

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