Cooperative Palladium and Copper Catalysis: One‐pot Synthesis of Diamino‐Substituted Naphthalenes from Aryl Halides, 1,4‐Bis(trimethylsilyl)butadiyne and Amines

Li, Yuan; Qiu, Shaozhong; Yin, Guodong

doi:10.1002/cctc.201901745

Cited by 7 publications

(9 citation statements)

References 48 publications

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“…If the substrate 1-bromo-4-methoxybenzene was used for the reaction, the yield of the product was very low, and it could not be isolated. This is attributed to the presence of an electron-donating group, which is unfavorable for nucleophilic attack 47 . iodide 156 begins with the addition of two equivalents of a ketone 157 in the presence of bimetallic palladium complex and silver triflate in 1,4 dioxane at 80 C for 1-2 h. Substrate scopes were examined for both aryl halide and ketone moiety to give the desired products in good yield.…”

Section: Synthesismentioning

confidence: 99%

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Hussain,

Maheshwari

2023

Synthesis

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This review article outlines the progress made in the synthesis of substituted naphthalene derivatives. Naphthalene and its derivatives exhibit various biological activities such as anti-inflammatory, anticancer, antiviral, antitubercular, antimicrobial, antihypertensive, antidiabetic, etc. Several strategies have been developed in the past for the construction of naphthalene derivatives, primarily focused on Metal-catalyzed reactions (palladium, copper, zinc, rhodium, platinum, nickel, etc.,) and Lewis acid-catalyzed transformations. This review discusses the preparations of naphthalene derivatives using various salt such as gallium chlorides, gold chlorides, gold bromides, various gold complexes as well as bronsted acids like triflic acid and trifluoroacetic acid, and Lewis acids such as like boron trifluoride etherate. Additionally, miscellaneous reactions involving metal and Lewis acids are explored. The transformational approaches covered in this review include cycloadditions, carboannulations, benzoannulations, electroannulations, rearrangements, and cross-dehydrogenative coupling reactions. Overall this review provides a comprehensive and up-to-date account of the current state of preparations of substituted naphthalenes, highlighting their medicinal and industrial importance.

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Section: Synthesismentioning

confidence: 99%

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Hussain,

Maheshwari

2023

Synthesis

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“…1,4-Bis(trimethylsilyl)-1,3-butadiyne was additionally employed as a precursor of compound ArC≡CC≡CAr in this type of transformation. A co-operative Pd/Cu catalytic system, enabling the initial double Sonogashira coupling of Me 3 SiC≡CC≡CSiMe 3 with aryl halides, was, in this case, used to generate the naphthalene products in a one-pot manner [112].…”

Section: Hydroamination and Hydroamidation Processesmentioning

confidence: 99%

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

Cadierno

2022

Catalysts

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Metal-catalyzed hydrofunctionalization reactions of alkynes, i.e., the addition of Y–H units (Y = heteroatom or carbon) across the carbon–carbon triple bond, have attracted enormous attention for decades since they allow the straightforward and atom-economic access to a wide variety of functionalized olefins and, in its intramolecular version, to relevant heterocyclic and carbocyclic compounds. Despite conjugated 1,3-diynes being considered key building blocks in synthetic organic chemistry, this particular class of alkynes has been much less employed in hydrofunctionalization reactions when compared to terminal or internal monoynes. The presence of two C≡C bonds in conjugated 1,3-diynes adds to the classical regio- and stereocontrol issues associated with the alkyne hydrofunctionalization processes’ other problems, such as the possibility to undergo 1,2-, 3,4-, or 1,4-monoadditions as well as double addition reactions, thus increasing the number of potential products that can be formed. In this review article, metal-catalyzed hydrofunctionalization reactions of these challenging substrates are comprehensively discussed.

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“…Compounds containing nitrogen heterocycles make up a significant portion of small drug molecules that have been approved by the Food and Drug Administration (FDA), amounting to approximately 60% [ 1 ]. Numerous new nitrogen heterocycles have been synthesized for their applications in biological and material sciences [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. Quinazoline is a frequently occurring structural feature in natural products and pharmaceutically active molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antibacterial, Antifungal and Anticorrosion Activities of 1,2,4-Triazolo[1,5-a]quinazolinone

et al. 2023

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The synthesis of 5,6,7,8-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-9(4H)-one (THTQ), a potentially biologically active compound, was pursued, and its structure was determined through a sequence of spectral analysis, including 1H-NMR, 13C-NMR, IR, and HRMS. Four bacterial and four fungal strains were evaluated for their susceptibility to the antibacterial and antifungal properties of the THTQ compound using the well diffusion method. The impact of THTQ on the corrosion of mild steel in a 1 M HCl solution was evaluated using various methods such as weight loss, potentiodynamic polarization (PDP), electrochemical impedance spectroscopy (EIS), and scanning electron microscopy (SEM) analysis. The study revealed that the effectiveness of THTQ as an inhibitor increased with the concentration but decreased with temperature. The PDP analysis suggested that THTQ acted as a mixed-type inhibitor, whereas the EIS data showed that it created a protective layer on the steel surface. This protective layer occurs due to the adsorption behavior of THTQ following Langmuir’s adsorption isotherm. The inhibition potential of THTQ is also predicted theoretically using DFT at B3LYP and Monte Carlo simulation.

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Cooperative Palladium and Copper Catalysis: One‐pot Synthesis of Diamino‐Substituted Naphthalenes from Aryl Halides, 1,4‐Bis(trimethylsilyl)butadiyne and Amines

Cited by 7 publications

References 48 publications

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

Synthesis, Characterization, Antibacterial, Antifungal and Anticorrosion Activities of 1,2,4-Triazolo[1,5-a]quinazolinone

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