51644-24-7

Upstream product

• 51-17-2 benzoimidazole 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 100-42-5 styrene 
• 42599-24-6 E-styryl iodide 
• 637-44-5 phenylpropyolic acid 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

L-proline promoted Ullmann-type reaction of vinyl bromides with imidazoles in ionic liquidst

The Ullmann-type coupling reaction of vinyl bromides and imidazoles in ILs at 90-110 °C gave the corresponding N-vinylimidazoles in good to excellent yields by using L-proline as the ligand; the double bond geometry of the vinyl bromides was retained under the reaction conditions. The Royal Society of Chemistry 2005.

Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base

Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre

Highly Chemo- and Regioselective Vinylation of N-Heteroarenes with Vinylsulfonium Salts

An efficient chemo- and regioselective N-vinylation of N-heteroarenes has been developed using vinylsulfonium salts. The reaction proceeded under mild and transition-metal-free conditions and consistently provided moderate to high yields of vinylation pro

Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions

A decarboxylative hydroamination cascade reaction of 3-arylpropiolic acids with N-heterocycles under transition-metal-free conditions was developed. 3-Arylpropiolic acids were found to react smoothly with a range of N-heterocycles under the effect of t-BuOK to afford N-vinyl heterocycles in moderate to excellent yields. This reaction represents the first decarboxylative hydroamination of 3-arylpropiolic acids without the aid of a transition-metal catalyst. Georg Thieme Verlag Stuttgart, New York.

Copper oxide nanoparticles catalyzed vinylation of imidazoles with vinyl halides under ligand-free conditions

Recyclable copper oxide nanoparticles catalyzed most efficient and straightforward protocol for the vinylation of imidazoles with vinyl halides under ligand-free conditions. Utilizing this protocol various imidazoles were cross-coupled with different substituted vinyl halides to get the corresponding products in excellent yields with the retention configuration.

Iron-catalyzed cross-coupling reaction of vinyl bromides or chlorides with imidazoles in the absence of ligands and additives

Highly effective coupling of imidazoles with (E)-vinyl halides can be achieved by using readily available iron catalysts under ligand-free, copper-free and palladium-free conditions. Coupling of (E)-vinyl bromides led to (Z)-products predominantly, while

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.

Cu2O-catalyzed Ullmann-type reaction of vinyl bromides with imidazole and benzimidazole

Cu2O was found to be an efficient and economical metal catalyst in the Ullmann cross-coupling reaction of vinyl bromides with imidazole or benzimidazole. The system Cu2O/ethyl 2-oxocyclohexanecarboxylate showed high catalytic activity in MeCN at 80-90 °C. The reaction gave the corresponding coupling products in good to excellent yields.

Mild Copper(I) iodide/β-keto ester catalyzed coupling reactions of styryl bromides with phenols, thiophenols, and imidazoles

An efficient and mild vinylation of O-, S-, and N-nucleophiles is reported. Copper(I) iodide/ethyl 2-oxocyclohexanecarboxylate is used as the catalytic system. The protocol tolerates a broad range of functional groups on the substrates, and gives the corr