Three-component Coupling Of Aldehydes Research Articles

First InCl3-Catalyzed, Three-Component Coupling of Aldehydes, β-Naphthol, and 6-Amino-1,3-dimethyluracil to Functionalized Naphthopyranopyrimidines

Indium(III) chloride was found to be a highly effective and efficient catalyst for the three-component, one-pot coupling of aldehydes, β-naphthol, and 6-amino-1,3-dimethyluracil under solvent-free conditions to give 8,10-dimethyl-12-aryl-12H-naphtho[1′,2′:5,6]pyrano[2,3-d]pyrimidine-9,11-diones in high yields for the first time. No co-catalyst or activator is required. Water and ammonia are the only byproducts in the reactions.

Magnetically separable Fe3O4 nanoparticles: an efficient catalyst for the synthesis of propargylamines

Abstract Magnetically separable Fe 3 O 4 nanoparticles endow with an efficient and economic route for the synthesis of propargylamines by the three-component coupling of aldehyde, amine, and alkyne through C–H activation. The reaction is especially effective for reactions involving aliphatic aldehydes and no additional co-catalyst or activator is required. High catalytic activity and ease of recovery using an external magnetic field are additional eco-friendly attributes of this catalytic system. The catalyst was recycled for five times without a significant loss of catalytic activity.

Three-component synthesis of 2-aryl-4-arylthio-tetrahydro-2 H-pyrans via the Prins-cyclization

A three-component coupling of aldehyde, homoallylic alcohol and aryl thiol has been achieved in the presence of trifluoroacetic acid in dichloromethane at room temperature to produce 4-arylthiotetrahydropyrans in good yields with all cis-selectivity. This method is simple, selective and convenient for introducing a thiol group on a tetrahydropyran ring.

Iodine-Catalyzed Three-Component Reaction: A Rapid Synthesis of α-Alkoxy Azides and Homoallyl Ethers

Iodine is found to be an efficient catalyst for the three-component coupling of aldehydes, alcohols, and TMSN 3 under mild and neutral conditions to provide α-alkoxy azides in good yields and with high selectivity. Allyltrimethylsilane also reacts rapidly with aldehydes in the presence of alcohols to produce homoallyl ethers under similar conditions. The use of iodine makes this procedure simple, convenient and cost-effective.

LiBr: A Mild Lewis Acid Catalyst for Efficient One-Pot Synthesis of α-Amino Nitriles

α-Amino nitriles are synthesized in a one-pot, three-component coupling of aldehydes, amines, and trimethylsilyl cyanide using a catalytic amount of LiBr at ambient temperature.

Reusable Polymer-Anchored Amino Acid Copper Complex for the Synthesis of Propargylamines

An amino acid was anchored to chloroacetylated polystyrene beads and the polymeric ligand containing N, O donor sites was treated with a solution of CuI to form the supported copper complex. The one-pot synthesis of propargylamines was then achieved efficiently via a three-component coupling of aldehydes, alkynes and amines using the supported copper catalyst under mild conditions. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity.

Three-Component Coupling of Aldehydes, Homoallyl Alcohols, and Trimethylsilyl Azide: A Facile Synthesis of 4-Azidotetrahydropyrans via the Prins Cyclization

The coupling of aldehydes, homoallylic alcohols, and trimethylsilyl azide has been achieved in the presence of phosphomo­lybdic acid (PMA) in dichloromethane to produce 4-azido- ­tetrahydropyran derivatives in high yields with all cis selectivity. The use of a heteropoly acid makes this procedure simple, convenient, and cost effective.

Synthesis of Propargylamines Catalyzed by Nanocrystalline Copper(II) Oxide

Three-component coupling of aldehydes 1, amines 2, and alkynes 3 took place in the presence of nanocrystalline copper oxide (nano CuO, 10 mol%; aldehyde:amine:alkyne = 1:1.3:1.5) to give the corresponding propargyl­amines 4 in up to 85% yield (15 examples). This catalyst was separated from the reaction mixture by centrifugation, and reused three times in the three-component coupling of benzaldehyde, piperidine, and phenylacetylene (76-82% yield).

Three-Component Coupling Reaction Using Silica-Immobilized CuI Catalyst

The three-component coupling of aldehydes, amines, and alkynes by using silica-immobilized CuI catalyst was described. Silica-supported copper catalyst SiO 2 -Py-CuI was prepared from 2-pyridylimine functionalized silica SiO 2 -Py with CuI in acetonitrile (eq. 1). The three-component coupling reactions of aldehydes, amines, and alkynes were carried out in the presence of 5 mol% silica-immobilized CuI catalyst SiO 2 -Py-CuI in ­acetonitrile at 90 °C to give the corresponding propargylamines in 54-93% yield (eq. 2).

In(OTf) 3-catalyzed synthesis of 4-thiocyanotetrahydropyrans via a three-component reaction

A three-component coupling of aldehydes, homoallylic alcohols and ammonium thiocyanate is achieved in the presence of 10 mol % of In(OTf) 3 in refluxing dichloromethane to produce 4-thiocyanotetrahydropyrans in excellent yields with all cis-selectivity. This method is simple, selective and convenient for introducing an SCN group onto a tetrahydropyran ring.

One-pot Efficient Synthesis of Cbz-protected β-Amino Ketones: Three-component Coupling of Aldehydes, Ketones, and Benzyl Carbamate

Abstract An efficient one-pot three-component reactions of aldehydes, ketones, and benzyl carbamate in the presence of a catalytic amount of (bromodimethyl)sulfonium bromide have been accomplished in short reaction time to afford the corresponding Cbz-protected β-amino ketones in high yields and good diastereoselectivity.

Silica-Immobilized CuI: An Efficient Reusable Catalyst for Three-Component Coupling Reaction of Aldehyde, Amine and Alkyne

: Silica-supported copper catalysts were effectively used in the three-component coupling of aldehydes, amines and alkynes to afford the corresponding propargylamines in moderate to excellent yields. The catalyst was quantitatively recovered from the reaction by a simple filtration and reused for a number of cycles with almost consistent activity.

Ultrasound-assisted one-pot approach to α-amino phosphonates under solvent-free and catalyst-free conditions

α-Amino phosphonates could be obtained in good to excellent yields by the three-component coupling of aldehydes, amines and diethylphosphite in one-pot procedure under ultrasound-assisted solvent-free and catalyst-free conditions.

A novel, practical and green synthesis of Ag nanoparticles catalyst and its application in three-component coupling of aldehyde, alkyne, and amine

Ag nanoparticles were synthesized in PEG with simple bubbling of H 2, and were used to catalyze the three-component coupling reaction of aldehyde, alkyne, and amine with good to excellent yields in one pot.

Molecular Iodine Catalyzed Imino‐Diels—Alder Reactions: Efficient One‐Pot Synthesis of Pyrano[3,2‐c]quinolines.

The successful use of molecular iodine as a catalyst in the intermolecular imino-Diels-Alder reaction is described. A one-pot synthesis of pyrano[3,2-c]quinolines was achieved by three-component coupling of aldehydes and anilines with 2,3-dihydropyran catalyzed by iodine. The reactions could be carried out smoothly at room temperature within three to six hours to offer the target products in good yields. We also investigated solvent effect, substituent effect, and the amount of iodine required.

Layered Double Hydroxide Supported Gold Catalyst for Three‐Component Aldehyde—Amine—Alkyne Coupling.

; A three-component coupling of aldehydes, amines and an alkyne to generate propargylic amines in nearly quantitative yields, using a layered double hydroxide-supported gold (LDH-AuCl 4 ) catalyst is described. Both aromatic and aliphatic aldehydes and amines are used for the reaction. No additional co-catalyst or activator is required.

Synthesis of Pentafluorophenylmethylamines via Silicon Mannich Reaction.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of Pentafluorophenylmethylamines via Silicon Mannich Reaction

[reaction: see text] The three-component coupling of aldehydes, secondary amines, and methoxytris(pentafluorophenyl)silane, MeOSi(C(6)F(5))(3), affording pentafluorophenylmethylamines has been described. The generation of the five-coordinate silicate intermediate is believed to be the key feature responsible for the efficiency of the reaction.

Molecular Iodine-Catalyzed Imino-Diels-Alder Reactions: Efficient One-Pot Synthesis of Pyrano[3,2-c]quinolines

The successful use of molecular iodine as a catalyst in the intermolecular imino-Diels-Alder reaction is described. A one-pot synthesis of pyrano[3,2-c]quinolines was achieved by three-component coupling of aldehydes and anilines with 2,3-dihydropyran catalyzed by iodine. The reactions could be carried out smoothly at room temperature within three to six hours to offer the target products in good yields. We also investigated solvent effect, substituent effect, and the amount of iodine required.

Layered Double Hydroxide-Supported Gold Catalyst for Three-Component Aldehyde-Amine-Alkyne Coupling

A three-component coupling of aldehydes, amines and an alkyne to generate propargylic amines in nearly quantitative yields, using a layered double hydroxide-supported gold (LDH-AuCl4) catalyst is described. Both aromatic and aliphatic aldehydes and amines are used for the reaction. No additional co-catalyst or activator is required.