Mannich Reaction In Water Research Articles

Organocatalyzed Mannich reaction: Electrochemically synthesized prolinated carbon dots vs. prolinated graphene oxide

Background L-Pro was previously used as an organocatalyst in the Mannich reaction under homogeneous conditions; a recoverable catalyst could be useful; this is the first report on the application of prolinated carbon dots to the Mannich reaction. Methods Prolinated carbon dots were synthesized electrochemically using a bottom-up approach; they were characterized and used in the Mannich reaction in water using only a slight excess of ketone; for a useful comparison, L-proline decorated graphene oxide was synthesized. Results The characterization of carbon dots and functionalized graphene oxide confirmed the presence of L-Pro on their surface; their use in the Mannich reaction gave good yields when carrying out the reaction in water; a possible recycle of the catalyst was demonstrated. Conclusions Both electrochemically synthesized prolinated carbon dots and prolinated graphene oxide acted as organocatalysts in the Mannich reaction. Higher yields were obtained using L-Pro-CDs obtained under galvanostatic conditions.

ChemInform Abstract: Broensted Acid‐Surfactant‐Combined Catalyst for the Mannich Reaction in Water.

Abstract3‐(N,N‐Dimethyloctylammonium) propanesulfonic acid tosylate, together with similar compounds, is synthesized and found to be a good and recyclable catalyst for the three‐component Mannich reaction.

Geminal Brønsted acid ionic liquids as catalysts for the Mannich reaction in water.

Quaternary ammonium geminal Brønsted acid ionic liquids (GBAILs) based on zwitterionic 1,2-bis[N-methyl-N-(3-sulfopropyl)-alkylammonium]ethane (where the carbon number of the alkyl chain is 4, 8, 10, 12, 14, 16, or 18) and p-toluenesulfonic acid monohydrate were synthesized. The catalytic ionic liquids were applied in three-component Mannich reactions with an aldehyde, ketone, and amine at 25 °C in water. The effects of the type and amount of catalyst and reaction time as well as the scope of the reaction were investigated. Results showed that GBAIL-C14 has excellent catalytic activity and fair reusability. The catalytic procedure was simple, and the catalyst could be recycled seven times via a simple separation process without noticeable decreases in catalytic activity.

Nano-manganese hydrogen sulfate as a novel catalyst for the anti-diastereoselective Mannich reaction in water

β-Amino carbonyl compounds are attractive targets for chemical synthesis, because they are widely used as biologically active compounds and are important synthons for a variety of pharmaceuticals. Nano-manganese hydrogen sulfate was prepared and used as a novel nano-catalyst for the named organic transformation, i.e. Mannich-type reaction of benzaldehyde, aniline, and cyclohexanone in water. Mannich products were obtained in high yields, with excellent diastereoselectivity, and short reaction time in the presence of a catalytic system comprising nano-Mn(HSO4)2 and a surfactant, for example sodium dodecyl sulfate. Use of mild, environmentally benign reaction conditions, low loading, and ready accessibility are the main features of this new catalyst.

A theoretical study of the nornicotine-catalyzed Mannich reaction in wet solvents and water

Quantum calculations lead the way to a green version of the versatile Mannich reaction in water catalysed by nornicotine.

One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)

A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature.

Brønsted acid-surfactant-combined catalyst for the Mannich reaction in water

A series of Bronsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N-dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity.

H5CoW12O40@nanosilica: a green, bifunctional, heterogeneous nanocatalyst for one-pot three-component Mannich reaction in water

12-Tungestocobaltic acid, H5CoW12O40, was immobilized on nanosilica from rice husk ash to produce H5CoW12O40@nanosilica as a bifunctional nanocatalyst. The TEM result showed that the particles are mostly spherical in shape, and that they have an average size of approximately 10 nm. The catalytic activity of this catalyst was investigated in Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally diverse β-amino ketones in high to excellent yields. Short reaction time, simple work-up procedure, elimination of toxic solvents, and low catalyst loading are the advantages of this procedure.

ChemInform Abstract: β‐Cyclodextrin‐Mediated Acetic Acid Catalyzed Diastereoselective Mannich Reaction in Water.

AbstractThe title reaction occurs in a syn‐selective fashion when propiophenone(III) is utilized as the ketone moiety, and in an anti selective manner when cyclohexanone (III) is utilized.

β-Cyclodextrin-Mediated Acetic Acid Catalyzed Diastereoselective Mannich Reaction in Water

A highly efficient diastereoselective Mannich reaction has been carried out in water using a catalytic amount of β-cyclodextrin as a chiral host in the presence of acetic acid to give the corresponding β-aminoketones (Mannich bases) with good yield (up to 98%) and excellent diastereomeric excess (up to >99%). This ­Bronsted acid–chiral cyclodextrin composite catalyzed reaction proceeds in a syn-selective manner with 98:2 syn/anti selectivity when propiophenone is used as the ketone moiety and in an anti-­selective manner with 100:0 (anti/syn) selectivity when cyclohexanone is used.

Aluminium dodecatungstophosphate (AlPW12O40)—An efficient catalyst for three-component Mannich reaction in water

One-pot, three-component Mannich reactions of ketones, aldehydes and amines were efficiently catalyzed by AlPW12O40 in water at ambient temperature to give the corresponding β-amino ketones in good to excellent yields. The method has the following merits: Firstly, Catalyst AlPW12O40 is non-corrosive and environmentally benign; Secondly, loading amount of catalyst is very low, less than 1 mol %; Thirdly, water as solvent is green and safe.

ChemInform Abstract: Synthesis and Structure of an Air‐Stable Organoantimony Complex and Its Use as a Catalyst for Direct Diastereoselective Mannich Reactions in Water

AbstractThe air‐stable organoantimony complex (I) is synthesized and used in the direct Mannich reaction in water under mild conditions.

ChemInform Abstract: Synthesis and Structure of an Air‐Stable Cationic Organobismuth Complex and Its Use as a Highly Efficient Catalyst for the Direct Diastereoselective Mannich Reaction in Water.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Lipase‐Catalyzed Direct Mannich Reaction in Water: Utilization of Biocatalytic Promiscuity for C—C Bond Formation in a “One‐Pot” Synthesis.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ga(OTf)3‐catalyzed Three‐component Mannich Reaction in Water Promoted by Ultrasound Irradiation

AbstractGa(OTf)3‐catalyzed three‐component Mannich reaction of aromatic aldehydes, aromatic amines and cycloketones in water promoted by ultrasound gave the corresponding β‐amino cycloketones in good to excellent yields and good anti selectivities.

Synthesis and structure of an air-stable cationic organobismuth complex and its use as a highly efficient catalyst for the direct diastereoselective Mannich reaction in water

An air-stable cationic organobismuth complex was successfully synthesized and found to show high catalytic efficiency in the direct diastereoselective Mannich reaction in water.

Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a “one-pot” synthesis

A novel lipase-catalysed direct Mannich reaction has been developed under aqueous conditions in a “one-pot” strategy. Interestingly, these promiscuous reactions can be greatly promoted by water and generally require aromatic aldehydes.

Mannich reaction in water using acidic ionic liquid as recoverable and reusable catalyst

The task-specific room-temperature ionic liquid (TSIL) N, N, N-trimethyl-N-butanesulfonic acid ammonium hydrogen sulfate [TMBSA]HSO4 was synthesized as a cheap and recyclable catalyst for one-pot three-component Mannich reaction in water. Sixteen β-amino carbonyl compounds were obtained in good yields under the mild conditions. The products could simply be separated from the catalyst/water, and the catalyst could be reused at least 7 times without noticeably decreasing the catalytic activity.

Highly Efficient One‐Pot Three‐Component Mannich Reaction in Water Catalyzed by Heteropoly Acids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Highly Efficient One-Pot Three-Component Mannich Reaction in Water Catalyzed by Heteropoly Acids

[reaction: see text] Heteropoly acids efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different amines in water at ambient temperature and afforded the corresponding beta-amino carbonyl compounds in good to excellent yields and with moderate diastereoselectivity. This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using very a small quantity of catalyst and a simple workup procedure.