scholarly journals Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5918
Author(s):  
Bimal Krishna Banik ◽  
Bubun Banerjee ◽  
Gurpreet Kaur ◽  
Shivam Saroch ◽  
Rajat Kumar
Keyword(s):  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Catalytic Amount ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Organic Transformations ◽  
Co Catalyst ◽  
Oxidation Reduction ◽  
Recent Developments ◽  
Significant Attention

During the last two decades, tetrabutylammonium bromide (TBAB) has gained significant attention as an efficient metal-free homogeneous phase-transfer catalyst. A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst for numerous coupling reactions. It has also acted as an efficient zwitterionic solvent in many organic transformations under molten conditions. In this review, we have summarized the recent developments on TBAB-catalyzed protocols for the efficient synthesis of various biologically promising heterocyclic scaffolds.

Rapid and efficient synthesis of metal-free phthalocyanine derivatives

2006 ◽  
Vol 10 (11) ◽  
pp. 1253-1258 ◽  
Author(s):  
Ahmad Shaabani ◽  
Ali Maleki
Keyword(s):  
Ionic Liquid ◽  
Microwave Irradiation ◽  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Efficient Synthesis ◽  
Metal Free ◽  
High Yields ◽  
Short Times

Metal-free phthalocyanine derivatives have been synthesized in very short times with high yields in the presence of 1,1,3,3-tetramethylguanidinium trifluoroacetate (TMGT) as an ionic liquid or tetrabutylammonium bromide (TBAB) as a phase transfer reagent under both classical heating conditions and using microwave irradiation. The best results were obtained with ionic liquid. Both the ionic liquid and phase transfer reagent can be recycled for subsequent reactions and reused without appreciable loss of efficiency.

scholarly journals Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5150
Author(s):  
Barbara Wołek ◽  
Mateusz Werłos ◽  
Magdalena Komander ◽  
Agnieszka Kudelko
Keyword(s):  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Fluorescence Emission ◽  
Cross Coupling ◽  
Solvent System ◽  
Quantum Yields ◽  
Coupling Reactions ◽  
Two Phase ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabutylammonium bromide, which plays the role of a phase-transfer catalyst. The luminescence properties of the obtained compounds are discussed in the context of applying these compounds in optoelectronics. Specifically, two highly-conjugated final products: N,N-dimethyl-2-phenyl-6-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)quinazolin-4-amine (8f) and 6,6′-(4,4′-(1,3,4-oxadiazole-2,5-diyl)bis(4,1-phenylene))bis(N,N-dimethylquinazolin-4-amine (9f), which contain a 1,3,4-oxadiazole moiety connected to a quinazoline ring by a 1,4-phenylene linker at the 6 position, exhibit strong fluorescence emission and high quantum yields.

Efficient Synthesis of Chromones with Alkenyl Functionalities by the Heck Reaction

2010 ◽  
Vol 63 (11) ◽  
pp. 1582 ◽  
Author(s):  
Tamás Patonay ◽  
Attila Vasas ◽  
Attila Kiss-Szikszai ◽  
Artur M. S. Silva ◽  
José A. S. Cavaleiro
Keyword(s):  
Heck Reaction ◽  
Halogen Atom ◽  
Phase Transfer ◽  
Bromine Atom ◽  
Tetrabutylammonium Bromide ◽  
Phase Transfer Catalyst ◽  
Efficient Synthesis ◽  
Terminal Alkenes

The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl‐substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine‐free conditions using a phase‐transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.

scholarly journals Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

2013 ◽  
Vol 9 ◽  
pp. 2470-2475 ◽  
Author(s):  
Ju Hee Kim ◽  
Su Jeong Choi ◽  
In Howa Jeong
Keyword(s):  
Cross Coupling ◽  
Catalytic Amount ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Cross Coupling Reactions ◽  
The Cross ◽  
High Yields

The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh3)2Cl2 and Na2CO3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3.

Core–shell nanoparticles: synthesis and applications in catalysis and electrocatalysis

2015 ◽  
Vol 44 (21) ◽  
pp. 7540-7590 ◽  
Author(s):  
Manoj B. Gawande ◽  
Anandarup Goswami ◽  
Tewodros Asefa ◽  
Huizhang Guo ◽  
Ankush V. Biradar ◽  
...  
Keyword(s):  
Oxygen Storage ◽  
Core Shell ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Shell Nanoparticles ◽  
Oxidation Reduction ◽  
Nanoparticles Synthesis ◽  
Core Shell Nanoparticles

Core–shell nanomaterials with a broad range of catalytic and electrocatalytic applications are summarized for an array of organic transformations namely oxidation, reduction, oxygen storage, and coupling reactions.

Nickel-Copper Co-Catalyzed Sustainable Synthesis of Diaryl- Chalcogenides

2021 ◽  
Vol 08 ◽  
Author(s):  
Debasish Kundu ◽  
Anup Roy ◽  
Abhijit Singha ◽  
Subir Panja
Keyword(s):  
Low Cost ◽  
Cross Coupling ◽  
Catalytic Amount ◽  
Metal Catalyst ◽  
Coupling Reactions ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Nickel Copper ◽  
Wide Range ◽  
Elimination Pathway

Abstract:: In recent times, Nickel has become a powerful alternative transition metal catalyst for performing cross-coupling reactions due to its low cost and better sustainability. Thus a sustainable Ni-catalyzed C-Se cross coupling has been developed in presence of catalytic amount of copper iodide as co-catalyst. A wide range of substituted diaryl selenides have been synthesized by this Ni-Cu dual catalyzed C-Se cross coupling. The reaction is following an oxidative addition and reductive elimination pathway where Cu is playing an important role in transmetalation. The mechanism of the reaction was established by several experimental techniques.

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Organocatalyzed Heterocyclic Transformations In Green Media: A Review

2020 ◽  
Vol 07 ◽  
Author(s):  
Neslihan Demirbas ◽  
Ahmet Demirbas
Keyword(s):  
Hydrogen Bonding ◽  
Phase Transfer ◽  
Noncovalent Interactions ◽  
Binding Capacity ◽  
Chemical Transformations ◽  
Organic Transformations ◽  
Phase Transfer Catalysts ◽  
Waste Production ◽  
Synthetic Methodologies ◽  
Organocatalytic Reactions

Background: Since the discovery of metal-free catalysts or organocatalysts about twenty years ago, a number of small molecules with different structures have been using to accelerate organic transformations. With the development of environmental awareness, in order to obtain highly privileged scaffolds, scientists have directed their studies towards the synthetic methodologies which minimize or preferably eliminate the formation of waste, avoid from toxic solvents and reagents and use renewable starting materials as far as possible. Methods: In this connection, the organocatalytic reactions providing efficiency and selectivity for most of case have become an endless topic in organic chemistry since several advantages from both practical and environmental standpoints. Organocatalysts supplying transformation of reactants into products with the least possible waste production have been serving to the concept of green chemistry. Results and Conclusion: Organocatalysts have been classified on the basis of their binding capacity to the substrate with covalently or noncovalent interactions involving hydrogen bonding and electrostatic interaction. Diverse types of small organic compounds including proline and its derivatives, phase-transfer catalysts, (thio)urease, phosphoric acids, sulfones, N-oxides, guanidines, cinchona derivatives, aminoindanol and amino acids have been utilized as hydrogen bonding organocatalysts in different chemical transformations.

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