Multi-Fold Sonogashira Coupling, A New Convenient Approach to Tetraalkynyl Anthracenes with Tunable Photophysical Properties

2021 ◽  
Author(s):  
Khadimul Islam ◽  
Himani Narjinari ◽  
AKSHARA BISARYA ◽  
Akshai Kumar
Keyword(s):  
Photophysical Properties ◽  
Single Step ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Convenient Approach ◽  
First Time

For the first time a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via the Pd(CH3CN)2Cl2/ cataCXium®A catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated...

scholarly journals Sulfur Versus Nitrogen Chelation in C-H Activation: Cobalt(III)-Catalyzed Unsymmetrical Double Annulation of Thioamides

2021 ◽  
Author(s):  
Majji Shankar ◽  
Arijit Saha ◽  
Somratan Sau ◽  
Arghadip Ghosh ◽  
Vincent Gandon ◽  
...  
Keyword(s):  
Density Functional ◽  
Chemical Space ◽  
Photophysical Properties ◽  
Structural Diversity ◽  
One Pot ◽  
Functional Theory ◽  
Biologically Relevant ◽  
Drug Candidates ◽  
Isoquinoline Derivatives ◽  
First Time

An unconventional cobalt(III)-catalyzed one-pot domino double annulation of aryl thioamides with unactivated alkynes is presented. Sulfur (S), nitrogen (N), and o,o'-C-H bonds of aryl thioamides are involved in this reaction, enabling access to rare 6,6-fused thiopyrano-isoquinoline derivatives. A reverse ‘S’ coordination over more conventional ‘N’ coordination of thioamides to Co-catalyst specifically regulates the formation of four [C-C and C-S at first and then C-N and C-C] bonds in a single operation, a concept which is uncovered for the first time. The power of the N-masked methyl phenyl sulfoximine (MPS) directing group in this annulation sequence is established. The transformation is successfully developed, building a novel chemical space of structural diversity (56 examples). In addition, late-stage annulation of biologically relevant motifs and drug candidates are disclosed (17 examples). Preliminary photophysical properties of thiopyrano-isoquinoline derivatives are discussed. Density functional theory (DFT) studies authenticate the participation of a unique 6p-electrocyclization of a 7-membered S-chelated cobaltacycle in the annulation process.<br>

scholarly journals Novel light-emitting clays with structural Tb3+ and Eu3+ for chromate anion detection

RSC Advances ◽  
2020 ◽  
Vol 10 (50) ◽  
pp. 29765-29771 ◽  
Author(s):  
Stefano Marchesi ◽  
Chiara Bisio ◽  
Fabio Carniato
Keyword(s):  
Photophysical Properties ◽  
Luminescent Materials ◽  
One Pot ◽  
Light Emitting ◽  
Anion Detection ◽  
Fluorescent Sensing ◽  
Chromate Anion ◽  
First Time ◽  
Synthetic Saponite

For the first time, Tb3+ and Eu3+ were incorporated into the framework of synthetic saponite by a one-pot hydrothermal procedure, obtaining luminescent materials with interesting photophysical properties, exploited for the fluorescent sensing of the chromate anion in water.

Facile One-Step Preparation and Efficient Photocatalytic Hydrogen Production of Composite MoS2/g-C3N4 Sensitized by Erythrosin B

NANO ◽  
2020 ◽  
Vol 15 (10) ◽  
pp. 2050127
Author(s):  
Mingcai Yin ◽  
Yixian Li ◽  
Kaiyue Liang ◽  
Jiangfan Sun ◽  
Yaoting Fan ◽  
...  
Keyword(s):  
Hydrogen Production ◽  
Photophysical Properties ◽  
Production Performance ◽  
One Pot ◽  
Photocatalytic Hydrogen Production ◽  
Erythrosin B ◽  
Production Activity ◽  
One Step ◽  
Calcination Method ◽  
First Time

MoS2/g-C3N4 (g-C3N4 [Formula: see text] graphitic carbon nitride) composite is considered as a promising photocatalyst for hydrogen production, while the preparation method still needs to be improved. Herein for the first time, nanosized MoS3 and melamine were used as starting materials and a facile one-pot calcination method was successfully applied for the synthesis of MoS2/g-C3N4. The physical and photophysical properties of the as-prepared MoS2/g-C3N4 were characterized by XRD, IR, SEM, TEM and XPS techniques. Sensitized by Erythrosin B (EB), the photocatalytic hydrogen production performance of MoS2/g-C3N4 was investigated and the amount of MoS2 was optimized. An excellent H2 production activity of 1091.2[Formula: see text][Formula: see text] was achieved for 43% MoS2/g-C3N4, which is about 330 times that of pure g-C3N4 (3.3[Formula: see text][Formula: see text]. In addition, its performance was compared with those of three other MoS2/g-C3N4 samples prepared by conventional methods and a possible mechanism of H2 production was proposed based on the photoluminescence and photoelectrochemical results.

scholarly journals Sulfur Versus Nitrogen Chelation in C-H Activation: Cobalt(III)-Catalyzed Unsymmetrical Double Annulation of Thioamides

2021 ◽  
Author(s):  
Majji Shankar ◽  
Arijit Saha ◽  
Somratan Sau ◽  
Arghadip Ghosh ◽  
Vincent Gandon ◽  
...  
Keyword(s):  
Density Functional ◽  
Chemical Space ◽  
Photophysical Properties ◽  
Structural Diversity ◽  
One Pot ◽  
Functional Theory ◽  
Biologically Relevant ◽  
Drug Candidates ◽  
Isoquinoline Derivatives ◽  
First Time

An unconventional cobalt(III)-catalyzed one-pot domino double annulation of aryl thioamides with unactivated alkynes is presented. Sulfur (S), nitrogen (N), and o,o'-C-H bonds of aryl thioamides are involved in this reaction, enabling access to rare 6,6-fused thiopyrano-isoquinoline derivatives. A reverse ‘S’ coordination over more conventional ‘N’ coordination of thioamides to Co-catalyst specifically regulates the formation of four [C-C and C-S at first and then C-N and C-C] bonds in a single operation, a concept which is uncovered for the first time. The power of the N-masked methyl phenyl sulfoximine (MPS) directing group in this annulation sequence is established. The transformation is successfully developed, building a novel chemical space of structural diversity (56 examples). In addition, late-stage annulation of biologically relevant motifs and drug candidates are disclosed (17 examples). Preliminary photophysical properties of thiopyrano-isoquinoline derivatives are discussed. Density functional theory (DFT) studies authenticate the participation of a unique 6p-electrocyclization of a 7-membered S-chelated cobaltacycle in the annulation process.<br>

scholarly journals Nickel-Catalyzed Deaminative Sonogashira Coupling of Alkylpyridinium Salts Enabled by a New NN2 Pincer Ligand

2020 ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Pincer Ligand ◽  
One Pot ◽  
Alkyl Amines ◽  
Sonogashira Reactions ◽  
First Time

Abstract Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Herein, a novel transformation is disclosed that enables the coupling of terminal alkynes with alkylpyridinium salts under Ni-catalysis. Key to the success of this coupling was the development of a new and readily accessible amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions for the first time, and leads to diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrates scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

An Expeditious One-Pot Three-Component Synthesis of 4-Aryl-3,4-dihydrobenzo[g] quinoline-2,5,10(1H)-triones under Green Conditions

2020 ◽  
Vol 23 (23) ◽  
pp. 2626-2634
Author(s):  
Saiedeh Kamalifar ◽  
Hamzeh Kiyani
Keyword(s):  
Reaction Medium ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
First Time ◽  
Green Conditions

: An efficient and facial one-pot synthesis of 4-aryl-3,4-dihydrobenzo[g]quinoline- 2,5,10(1H)-triones was developed for the first time. The process proceeded via the three-component cyclocondensation of 2-amino-1,4-naphthoquinone with Meldrum’s acid and substituted benzaldehydes under green conditions. The fused 3,4-dihydropyridin-2(1H)- one-ring naphthoquinones have been synthesized with good to high yields in refluxing ethanol as a green reaction medium. This protocol is simple and effective as well as does not involve the assistance of the catalyst, additive, or hazardous solvents.

Microwave-accelerated Carbon-carbon and Carbon-heteroatom Bond Formation via Multi-component Reactions: A Brief Overview

2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Cycloaddition Reaction ◽  
Nanoparticle Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
One Pot ◽  
Bond Forming ◽  
Material Interest ◽  
Carbon Carbon Bond

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.

Six-Sided Heptaporphyrin Array: Towards a Nano-Sized Cube

2004 ◽  
Vol 69 (5) ◽  
pp. 996-1008 ◽  
Author(s):  
Steven J. Langford ◽  
Clint P. Woodward
Keyword(s):  
Single Step ◽  
One Pot ◽  
H Nmr ◽  
The Core ◽  
Nmr Techniques ◽  
Axial Vertex

A strategy in preparing a family of hexameric porphyrin cubes based on the interplay of Sn(IV)-O and Ru(II)-N interactions is described. In this first iteration, we have prepared the heptamer [SnIV(TPyP)·(4)2][Ru(CO)(TPP)]6 (4 = (E)-(3-(4-pyridyl)acrylate)) constituting a 5,10,15,20-tetra(4-pyridyl)porphyrin (TPyP) core and 5,10,15,20-tetraphenylporphyrin (TPP) faces and compared its formation by stepwise and "one-pot" strategies where up to nine components are assembled in a single step in a regiospecific manner. In one example, the heptamer is formed around the template [SnIV(TPyP)·(4)2] bearing pyridine groups in which the nitrogens radiate octahedrally along each vertex. The ability to modulate the axial vertex through choice of pyridine is also demonstrated. 1H NMR measurements on [SnIV(TPyP)·(4)2][Ru(CO)(TPP)]6 indicate that the protons on the core template are extremely shielded as a result of the anisotropy of the peripheral porphyrin units. Various NMR techniques, including NOESY experiments, have been used to characterise the heptamer in solution.

scholarly journals Broad scope gold(i)-catalysed polyenyne cyclisations for the formation of up to four carbon–carbon bonds

2017 ◽  
Vol 15 (10) ◽  
pp. 2163-2167 ◽  
Author(s):  
Zhouting Rong ◽  
Antonio M. Echavarren
Keyword(s):  
Single Step ◽  
Simultaneous Formation ◽  
Broad Scope ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
First Time ◽  
High Stereoselectivity

The polycyclisation of polyeneynes catalyzed by gold(i) has been extended for the first time to the simultaneous formation of up to four carbon–carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings.

scholarly journals One-Pot Hydrothermal Synthesis of Victoria Green (Ca3Cr2Si3O12) Nanoparticles in Alkaline Fluids and Its Colour Hue Characterisation

Nanomaterials ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 521
Author(s):  
Juan Carlos Rendón-Angeles ◽  
Zully Matamoros-Veloza ◽  
Jose Luis Rodríguez-Galicia ◽  
Gimyeong Seong ◽  
Kazumichi Yanagisawa ◽  
...  
Keyword(s):  
Near Infrared ◽  
Single Step ◽  
Spectral Space ◽  
Infrared Reflectance ◽  
Hydrothermal Preparation ◽  
Near Infrared Reflectance ◽  
One Pot ◽  
Factors Affecting ◽  
B Values ◽  
Alkaline Conditions

One-pot hydrothermal preparation of Ca3Cr2Si3O12 uvarovite nanoparticles under alkaline conditions was investigated for the first time. The experimental parameters selected for the study considered the concentration of the KOH solvent solution (0.01 to 5.0 M), the agitation of the autoclave (50 rpm), and the nominal content of Si4+ (2.2–3.0 mole). Fine uvarovite particles were synthesised at 200 °C after a 3 h interval in a highly concentrated 5.0 M KOH solution. The crystallisation of single-phase Ca3Cr2Si3O12 particles proceeded free of by-products via a one-pot process involving a single-step reaction. KOH solutions below 2.5 M and water hindered the crystallisation of the Ca3Cr2Si3O12 particles. The hydrothermal treatments carried out with stirring (50 rpm) and non-stirring triggered the crystallisation of irregular anhedral particles with average sizes of 8.05 and 12.25 nm, respectively. These particles spontaneously assembled into popcorn-shaped agglomerates with sizes varying from 66 to 156 nm. All the powders prepared by the present method exhibited CIE-L*a*b* values that correspond to the Victoria green colour spectral space and have a high near infrared reflectance property. The particle size and structural crystallinity are factors affecting the Victoria pigment optical properties, such as CIE-L*a*b* values, green tonality, and near-infrared reflectance.

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