82489-29-0

Upstream product

• 61582-64-7 N,N-diethyl-O-benzoylhydroxylamine 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 55606-20-7 (E)-N-styrylpiperidine 
• 39166-25-1 (E)-N-(2-phenylethenyl)morpholine 
• 109-89-7 diethylamine 
• 122-78-1 phenylacetaldehyde 
• 536-74-3 phenylacetylene 
• 2431-96-1 N,N-diethylphenylacetamide 
• 100-42-5 styrene 
• 1566-67-2 (Z)-styryl acetate 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 76512-46-4 ethyl 4-oxo-5-phenyl-4H-pyran-2-carboxylate 
• 77831-63-1 4-Diethylamino-3-phenyl-3-buten-2-one 
• 59591-39-8 5-phenyl-3-(3-trifluoromethyl-phenyl)-1H-pyridazin-4-one 
• 59591-40-1 1-methyl-5-phenyl-3-(3-trifluoromethyl-phenyl)-1H-pyridazin-4-one 
• 39166-25-1 (E)-N-(2-phenylethenyl)morpholine 
• 122-78-1 phenylacetaldehyde 
• 55606-20-7 (E)-N-styrylpiperidine 
• 84395-76-6 (E)-N-benzyl-N-methyl-2-phenylethen-1-amine 
• 6908-73-2 (E)-1-styrylpyrrolidine 
• 5300-21-0 N,N-diethylphenethylamine 
• 1235304-71-8 2-(diethylamino)-3,3-difluoro-3-phenylpropanenitrile 
• 1235304-70-7 2-(diethylamino)-3-fluoro-3-phenylpropanenitrile 
• 59756-85-3 3-(3-benzyloxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 

Relevant academic research and scientific papers

Iridium-PPh3 Catalysts for Conversion of Amides to Enamines

Studies on the deactivation mechanism of the reaction of N,N-dialkylamides with TMDS catalyzed by Vaska's complex, IrCl(CO)(PPh3)2 (1a), triggered the discovery of highly active Ir-PPh3 catalysts: Photochemically activated

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.

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.

Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

The appropriate design of a ligand (L) in IrCl(CO)(L)2 (4) realized the efficient synthesis of π-conjugated enamines possessing hole-transport properties. The iridium complex with electron-withdrawing phosphorus ligands catalyzed the hydrosilylation of amides to the corresponding silylhemiaminals, which were transformed to the enamines by heat or by treatment with acids. High catalytic efficiency (TON > 10,000) was achieved, which made it possible for the residual iridium in the enamine product to be below 20 ppb.

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.

Formal anti-markovnikov hydroamination of terminal aryl alkynes with pinacolborane and hydroxylamines via Zr/Cu sequential catalysis

We have explored a novel dry plasma process for the fabrication of electrodes on Nafion surfaces. Nanosized pillar structures were prepared through argon ion (Ar+) plasma treatment. The shear strengths of Au electrodes on plasma-treated Nafion surfaces were investigated. We found that the maximum shear strength (1.08 MPa) of Au-Nafion was observed under the optimal conditions (8 min, 100 W, 5 Pa, Ar+). Finally, we successfully prepared strongly bonded Au electrodes on Nafion through plasma surface treatment without using a wet plating process.

Hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex-catalyzed addition of β-diketones to 1-alkynes and anti-markovnikov addition of secondary amines to aromatic 1-alkynes

The hydro(trispyrazolyl)borato-ruthenium(II) diphosphinoamino complex TpRu[4-CF3C6H4N(PPh2) 2](OTf) (I) [Tp=hydro(trispyrazolyl)borate] catalyzes the Markovnikov addition of β-diketones to unactivated 1-alkynes in good to excellent yields. The reaction proceeds under solvent-free and additive-free conditions and the catalyst loading can be reduced down to 0.4amol%. Complex I (1amol%) also catalyzes the addition of secondary amines to aromatic terminal alkynes, unusual anti-Markovnikov products are exclusively formed.

Highly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditions

The combination of IrCl(CO)(PPh3)2 with 1,1,3,3-tetramethyldisiloxane or poly(methylhydrosiloxane) (PMHS) is found to be an efficient catalyst system for the preparation of aldenamines from carboxamides; in particular, facile removal of silicone and iridium residues from the product can be achieved by the use of PMHS.

A polymer-bound oxidovanadium(IV) complex prepared from an L-cysteine-derived ligand for the oxidative amination of styrene

The ligand H2sal-cys (I) derived from salicylaldehyde and Lcysteine has been covalently bonded to chloromethylated polystyrene cross-linked with 5% divinylbenzene. Upon treatment with [VO(acac)2] in dimethylformamide (DMF) the polystyrene-bound ligand PS-H2sal-cys (II) gave the oxidovanadium(IV) complex, PS-[VO(sal-cys)·DMF] (1). The corresponding neat complex, [VO(sal-eta)]2 (2), has also been prepared similarly in methanol. These complexes have been characterised by IR, electronic, EPR spectroscopic studies, magnetic susceptibility measurements and thermal as well as scanning electron micrographs studies. Complex [VO-(sal-eta)]2 exhibits a medium intensity band at 980 cm -1 in the IR spectrum due to ν(V=O) stretch. Broad features of the EPR spectrum for the neat complex along with magnetic susceptibility studies suggest the presence of antiferromagnetic exchange interaction between two vanadium centers in close proximity. Both complexes catalyze the oxidative amination of styrene, in mild basic conditions, with secondary amines (diethylamine, imidazole, and benzimidazole) and gave a mixture of two aminated products in good yields. Amongst the two aminated products, the anti-Markovnikov product is favored over the Markovnikov one due to the steric hindrance posed by the secondary amines. The polymeranchored heterogeneous catalyst is free from leaching during catalytic action and recyclable. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Highly chemoselective formation of aldehyde enamines under very mild reaction conditions

Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfull