N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions

2016 ◽  
Vol 52 (51) ◽  
pp. 7958-7961 ◽  
Author(s):  
Marcus Blümel ◽  
Reece D. Crocker ◽  
Jason B. Harper ◽  
Dieter Enders ◽  
Thanh V. Nguyen
Keyword(s):  
Phase Transfer ◽  
Solid Phase ◽  
Alkylation Reaction ◽  
Phase Transfer Catalysts ◽  
Wide Range ◽  
Alkylation Reactions

N-Heterocyclic olefins (NHOs) chemically transfer the base from solid phase and promote alkylation reaction on a wide range of substrates.

scholarly journals Synthesis of cationic dibenzosemibullvalene-based phase-transfer catalysts by di-π-methane rearrangements of pyrrolinium-annelated dibenzobarrelene derivatives

2011 ◽  
Vol 7 ◽  
pp. 119-126 ◽  
Author(s):  
Heiko Ihmels ◽  
Jia Luo
Keyword(s):  
Solid State ◽  
Nitrogen Atom ◽  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Covalent Attachment ◽  
Phase Transfer Catalysts ◽  
Counter Ion ◽  
Alkylation Reactions

Dibenzobarrelene derivatives, that are annelated with a pyrrolinium unit [N,N-dialkyl-3,4-(9',10'-dihydro-9',10'-anthraceno-3-pyrrolinium) derivatives], undergo a photo-induced di-π-methane rearrangement upon triplet sensitization to give the corresponding cationic dibenzosemibullvalene derivatives [N,N-dialkyl-3,4-{8c,8e-(4b,8b-dihydrodibenzo[a,f]cyclopropa[cd]pentaleno)}pyrrolidinium derivatives]. Whereas the covalent attachment of a benzophenone functionality to the pyrrolinium nitrogen atom did not result in an internal triplet sensitization, the introduction of a benzophenone unit as part of the counter ion enables the di-π-methane rearrangement of the dibenzobarrelene derivative in the solid-state. Preliminary experiments indicate that a cationic pyrrolidinium-annelated dibenzosemibullvalene may act as phase-transfer catalyst in alkylation reactions.

Highly enantioselective asymmetric Henry reaction catalyzed by novel chiral phase transfer catalysts derived from cinchona alkaloids

2016 ◽  
Vol 14 (42) ◽  
pp. 10101-10109 ◽  
Author(s):  
Ponmuthu Kottala Vijaya ◽  
Sepperumal Murugesan ◽  
Ayyanar Siva
Keyword(s):  
Phase Transfer ◽  
Enantiomeric Excess ◽  
Cinchona Alkaloids ◽  
Henry Reaction ◽  
Reaction Conditions ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Wide Range ◽  
Chiral Phase Transfer Catalysts

Newly synthesized CPTCs are applied in the asymmetric Henry reaction to a wide range of aldehydes under mild reaction conditions, and we obtained higher chemical yields and an excellent enantiomeric excess.

ChemInform Abstract: N-Heterocyclic Olefins as Efficient Phase-Transfer Catalysts for Base-Promoted Alkylation Reactions.

ChemInform ◽  
2016 ◽  
Vol 47 (44) ◽  
Author(s):  
Marcus Bluemel ◽  
Reece D. Crocker ◽  
Jason B. Harper ◽  
Dieter Enders ◽  
Thanh V. Nguyen
Keyword(s):  
Phase Transfer ◽  
Phase Transfer Catalysts ◽  
Alkylation Reactions

scholarly journals Alkylation of N-substituted 2-phenylacetamides: Benzylation of N-(4-chlorophenyl)-2-phenylacetamide

2004 ◽  
Vol 69 (2) ◽  
pp. 85-92 ◽  
Author(s):  
Dusan Mijin ◽  
Vida Jankovic ◽  
Slobodan Petrovic
Keyword(s):  
Gas Chromatography ◽  
Potassium Hydroxide ◽  
Benzyl Chloride ◽  
Phase Transfer ◽  
Alkylation Reaction ◽  
Reaction Products ◽  
Reaction Conditions ◽  
Phase Transfer Catalysts ◽  
Different Temperatures

Benzylation of N-(4-chlorophenyl)-2-phenylacetamidewith benzyl chloride in the presence of powdered potassium hydroxide under various reaction conditions was performed in order to establish the possible reaction products. Different temperatures and ratios of reactants and solvents were used. The reactions were also carried out in the presence of different phase-transfer catalysts in toluene as a solvent. The formation of the reaction products was followed using gas chromatography. On the basis of the obtained results, the reactivity and the orientation in the alkylation reaction of the investigated amide is discussed.

ANIONIC ION EXCHANGERS AS PHASE TRANSFER CATALYSTS IN ALKYLATION REACTIONS

1997 ◽  
pp. 87-95 ◽  
Author(s):  
Fernando Varona ◽  
Federico Mijangos ◽  
Jose I. Lombraña ◽  
Mario Díaz
Keyword(s):  
Phase Transfer ◽  
Ion Exchangers ◽  
Phase Transfer Catalysts ◽  
Alkylation Reactions

Analysis of Aromatic Amines in Industrial Wastewater by Capillary Gas Chromatography-Mass Spectrometry

2000 ◽  
Vol 35 (2) ◽  
pp. 245-262 ◽  
Author(s):  
Francis I. Onuska ◽  
Ken A. Terry ◽  
R. James Maguire
Keyword(s):  
Gas Chromatography ◽  
Aromatic Amines ◽  
Methylene Chloride ◽  
Solid Phase ◽  
Stationary Phases ◽  
Gas Chromatography Mass Spectrometry ◽  
Substituted Anilines ◽  
Environmental Media ◽  
Solid Phase Extraction Cartridge ◽  
Wide Range

Abstract The analysis of aromatic amines, particularly benzidines, at trace levels in environmental media has been difficult because of the lack of suitable deactivated capillary column stationary phases for gas chromatography. This report describes the use of an improved type of column as well as a method for the analysis of anilines and benzidines in water, wastewater and sewage samples. Extraction procedures are applicable to a wide range of compounds that are effectively partitioned from an aqueous matrix into methylene chloride, or onto a solid-phase extraction cartridge. The extracted analytes are also amenable to separation on a capillary gas chromatographic column and transferable to the mass spectrometer. These contaminants are converted to their N-trifluoroacetyl derivatives. Aniline and some substituted anilines, and 3,3’-dichlorobenzidine and benzidine were determined in 24-h composite industrial water, wastewater, primary sludge and final effluent samples at concentrations from 0.03 up to 2760 µg/L.

Recent Application of Polystyrene-supported Triphenylphosphine in Solid-Phase Organic Synthesis

2019 ◽  
Vol 23 (6) ◽  
pp. 643-678
Author(s):  
Lalthazuala Rokhum ◽  
Ghanashyam Bez
Keyword(s):  
Organic Synthesis ◽  
Combinatorial Chemistry ◽  
Solid Phase ◽  
Recent Application ◽  
Organic Transformations ◽  
Solid Phase Organic Synthesis ◽  
Wide Range ◽  
Fast Development ◽  
Polymer Supported

Recent years have witnessed a fast development of solid phase synthetic pathways, a variety of solid-supported reagent and its applications in diverse synthetic strategies and pharmaceutical applicability’s. Polymer-supported triphenylphosphine is getting a lot of applications owing to the speed and simplicity in the process. Furthermore, ease of recyclability and reuse of polymer-supported triphenylphosphine added its advantages. This review covers a wide range of useful organic transformations which are accomplished using cross-linked polystyrene-supported triphenylphosphine with the aim of giving renewed interest in the field of organic and medicinal-combinatorial chemistry.

Green Application of Phase-Transfer Catalysis in Oxidation: A Comprehensive Review

2020 ◽  
Vol 17 (4) ◽  
pp. 405-411
Author(s):  
Chuan-Hui Wang ◽  
Chen-Fu Liu ◽  
Guo-Wu Rao
Keyword(s):  
Organic Chemistry ◽  
Green Chemistry ◽  
Oxidation Reaction ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Important Application ◽  
Oxidation Reactions ◽  
Comprehensive Review ◽  
Phase Transfer Catalysts ◽  
Onium Salts

Oxidation reactions have emerged as one of the most versatile tools in organic chemistry. Various onium salts such as ammonium, phosphonium, arsonium, bismuthonium, tellurium have been used as phase transfer catalysts in many oxidation reactions. Certainly, considerable catalysts have been widely used in Phase-Transfer Catalysis (PTC). This review focuses on the application of PTC in various oxidation reaction. Furthermore, PTC also conforms to the concept of “Green Chemistry”. <p></p> • Oxidation has become one of the most widely used tools in organic chemistry and phase transfer catalysts has been widely used in oxidation. <p></p> • The application of phase transfer catalysts in oxidation reaction will be summarized. <p></p> • Phase transfer catalysts have important application in various oxidation reaction.

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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