55606-20-7

Upstream product

• 57675-90-8 1-(2,2,2-trichloro-ethyl)-piperidine 
• 591-51-5 phenyllithium 
• 110-89-4 piperidine 
• 100-42-5 styrene 
• 1566-67-2 (Z)-styryl acetate 
• 536-74-3 phenylacetylene 
• 3626-62-8 2-phenyl-1-(1-piperidinyl)ethanone 
• 82489-29-0 (E)-N,N-diethyl-2-phenylethen-1-amine 
• 39166-25-1 (E)-N-(2-phenylethenyl)morpholine 
• 103-80-0 phenylacetyl chloride 
• 128010-34-4 N-Piperidino-α-phenylselenoacetamide 
• 95038-61-2 (piperidin-1-ylmethyl)diphenylphosphine oxide 
• 100-52-7 benzaldehyde 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 7114-36-5 phenyl-piperidin-1-yl-acetaldehyde 
• 332-14-9 1-phenethylpiperidine 
• 2016-03-7 2,3-diphenylpropanal 
• 39166-25-1 (E)-N-(2-phenylethenyl)morpholine 
• 122-78-1 phenylacetaldehyde 
• 82489-29-0 (E)-N,N-diethyl-2-phenylethen-1-amine 
• 84395-76-6 (E)-N-benzyl-N-methyl-2-phenylethen-1-amine 
• 6908-73-2 (E)-1-styrylpyrrolidine 

Relevant academic research and scientific papers

Intermolecular hydroamination versus stereoregular polymerization of phenylacetylene by rhodium catalysts based on N-O bidentate ligands

N-O bidentate ligands, such as 8-quinolinol and aminoacids, in combination with the dinuclear precursor [{Rh(μ-OMe)(COD)}2] are versatile catalytic systems. Thus, stereoregular polymerization of phenylacetylene (PA) is observed in the presence

Hydrogen-Bond-Promoted Metal-Free Hydroamination of Alkynes

An original metal-free regio- A nd stereoselective intermolecular hydroamination of alkynes is described. Various (E)-enamines were obtained from arylacetylenes and aliphatic secondary amines in the presence of ethylene glycol as a solvent. The latter is

Dynamic Covalent Chemistry of Aldehyde Enamines: BiIII- and ScIII-Catalysis of Amine–Enamine Exchange

The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)3 and Sc(OTf)3 (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with 2 % by-product formation within one week after complete equilibration. This study expands the scope of dynamic C?N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.

The pyrrole ring η2-hapticity bridged binuclear tricarbonyl Mo(0) and W(0) complexes: catalysis of regioselective hydroamination reactions and DFT calculations

Following the report of the ferrocene structure, metal complexes containing the heteroatom-substituted cyclopentadienyl (Cp) analogue, that is the η5 pyrrolyl ligand, have been reported. While the Cp ligand continues to be a favorite ligand in

An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides

A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).

Facile preparation of pyrimidinediones and thioacrylamides: Via reductive functionalization of amides

The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by

Synthesis and Reactivity of Phosphine-Quinolinolato Rhodium Complexes: Intermediacy of Vinylidene and (Amino)carbene Complexes in the Catalytic Hydroamination of Terminal Alkynes

We report here on the syntheses of rhodium(I) complexes bearing a phosphine-quinolinolate ligand and the isolation of two classes of important intermediates in the anti-Markovnikov hydroamination of terminal alkynes with secondary amines: vinylidene-bridged dirhodium complexes and (amino)carbene complexes. We first prepared various rhodium(I) complexes bearing a phosphine-quinolinolate ligand and found that some of these complexes had catalytic activity for the anti-Markovnikov hydroamination of terminal alkynes with secondary amines. The reaction of stoichiometric amounts of a (PNO)Rh complex with terminal alkynes provided vinylidene-bridged dirhodium complexes. When the resulting vinylidene complexes were reacted with secondary amines, (amino)carbene complexes were generated, which gave the hydroamination product upon heating with an additive. These results suggest that this anti-Markovnikov hydroamination catalyzed by (PNO)Rh complexes proceeds via vinylidene and (amino)carbene complexes.

1,3-Dipolar cycloaddition reactivities of perfluorinated aryl azides with enamines and strained dipolarophiles

The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamine-azide cycloadditions.

Hydroamination of terminal alkynes with secondary amines catalyzed by copper: Regioselective access to amines

A simple and convenient copper-catalyzed hydroamination of arylacetylenes with secondary amines has been performed giving a simple access to aliphatic amines after reduction of the hydroaminated products (E-enamines). Here we described a mild catalytic system utilizing CuCN precatalyst without any additive ligands in a solvent-free system.

Efficient and selective synthesis of e-vinylamines via tungsten(0)-catalyzed hydroamination of terminal alkynes

The hydroamination of terminal alkynes (RC≡CH=phenylacetylene, 4-methylphenylacetylene, 4-fluorophenylacetylene, 1-hexyne, methyl 2-propynyl ether, prop-2-yn-1-ol) with secondary amines (piperidine, pyrrolidine, morpholine, piperazine, methylpiperazine, 4