14064-35-8

Upstream product

• 24964-64-5 3-Cyanobenzaldehyde 
• 13246-50-9 benzylchlorotriphenylphosphorane 
• 24722-19-8 3-[(1,1,1-triphenylphosphonio)methyl]benzonitrile bromide 
• 100-52-7 benzaldehyde 
• 6952-59-6 3-cyanobromobenzene 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-42-5 styrene 
• 1589517-61-2 (Z)-3-(1-bromo-2-phenylvinyl)benzonitrile 
• 766-84-7 3-chloro-benzonitrile 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 64-19-7 acetic acid 

Downstream Products

• 103119-19-3 Trans-3-(1'hydroxyhexyl) Stilbene 
• 103119-18-2 trans-3-hexanoylstilbene 

Relevant academic research and scientific papers

Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides

Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.

A Bis (BICAAC) Palladium(II) Complex: Synthesis and Implementation as Catalyst in Heck-Mizoroki and Suzuki-Miyaura Cross Coupling Reactions

Carbenes are one of the most appealing, well-explored, and exciting ligands in modern chemistry due to their tunable stereoelectronic properties and a wide area of applications. A palladium complex (BICAAC)2PdCl2 with a recently discovered cyclic (alkyl)(amino)carbene having bicyclo[2.2.2] octane skeleton (BICAAC) was synthesized and characterized. The enhanced σ-donating and π-accepting ability of this carbene lend a hand to form a robust Pd-carbene bond, which allowed us to probe its reactivity as a precatalyst in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions with low catalyst loading in open-air conditions. The diverse range of substrates was explored for both the cross-coupling reactions. To get a better understanding of the catalytic reactions, several analytical techniques such as field-emission scanning electron microscopy, high-resolution transmission electron microscopy, and powder X-ray diffraction were employed in a conclusive manner.

Mizoroki-Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards

The potential safety hazards associated with the Mizoroki-Heck cross-coupling of bromobenzenes with styrenes were evaluated. The heat output from the reaction in various solvents was comparable in a variety of solvents; however, the rate of reaction was significantly faster in the presence of water. Thermal stability evaluation of the postreaction mixtures in DMSO and 3:1 DMSO/water by differential scanning calorimetry indicated that the onset temperatures of thermal decomposition were significantly lower than that of neat DMSO. Evaluation of the substrate scope revealed that the substitution pattern on the bromobenzene did not affect the heat output. The reaction rate of electron-deficient bromobenzenes was slower than that of the electron-rich bromobenzenes. In general, substituted styrenes afforded similar magnitudes of exotherms; however, the reaction rate of bromobenzene with 2-methylstyrene was significantly slower than the other studied styrenes. The predicted heat of reaction using the density functional theory method, B3LYP, was in good agreement with the experimental data. Such excellent agreement suggests that this calculation method can be used as a preliminary tool to predict heat of reaction and avoid exothermic reaction conditions. In many of the studied cases, the maximum temperature of a synthesis reaction was considerably higher than the solvent boiling point and thermal decomposition onset temperatures when the reaction was performed in DMSO or 3:1 DMSO/water. It is crucial to understand the thermal stability of the reaction mixture to design the process accordingly and ensure the reaction temperature is maintained below the onset temperature of decomposition to avoid potential runaway reactions.

Tetranuclear Palladium Complexes of Abnormal N-Heterocyclic Carbene Ligands and their Catalytic Activities in Mizoroki-Heck Coupling Reaction of Electron-Rich Aryl Chlorides

Based on the ligand scaffold of an imidazolyl/benziimidazolyl moiety and a N-CH2C(=O)NHPh substituent, two series of ligand precursors with ortho hydroxy groups incorporated on the N-phenyl rings were prepared. The structural fine tuning of the ligand scaffold allowed the synthesis of tetranuclear palladium complexes with abnormal N-heterocyclic carbene (aNHC) ligands. For precursors with C2-methyl blocking groups, pyridine-assisted C?H bond activation led to the formation of mononuclear tridentate palladium aNHC complexes or tetranuclear complexes with tridentate CNO donors. Representative mononuclear and tetranuclearpalladium aNHC complexes were structurally characterized by X-ray diffraction studies, revealing very short Pd?C bond distances. The tetranuclear palladium aNHC complexes were very effective in catalyzing Mizoroki-Heck coupling reaction, and were capable of employing a range of aryl chlorides including deactivated substrates with low palladium loading of 0.2 mol%. (Figure presented.).

Synthesis of 1,2-diarylethylenes by Pd-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes

Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances. Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields. Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes. Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

Rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes

A rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.

Stereospecific hydrodehalogenation of alkenyl bromides: A new approach to the synthesis of (E)-alkenes

The pair NaBH4-TMEDA and catalytic PdCl2(PPh 3)2 in THF at room temperature is a mild and efficient system for the hydrodebromination of alkenyl bromides, providing a facile reduction procedure that allows completing the process advantageously, leading from aldehydes to (E)-alkenes. This journal is the Partner Organisations 2014.

Design, synthesis and in vitro biological evaluation of 3-styrylbenzimidamides as potential BACE1 inhibitors

A series of 3-styrylbenzimidamides were synthesized and biologically evaluated in a cell free FRET assay as potential BACE1 inhibitors. Some of the synthesized analogues were discovered to have moderate BACE1 inhibitory activities with IC50 values ranging

A robust first-pass protocol for the heck-mizoroki reaction

The Heck-Mizoroki (HM) reaction is one of the most widely used C-C bond-forming methods of contemporary synthesis. Notwithstanding this, these reactions frequently require significant optimization before efficient transformations can be obtained. We describe here the results of a study that aimed to establish a generic experimental protocol for HM reactions which enables acceptable yields from first-pass experiments. The methodology utilizes readily available stable catalysts and can be applied to a broad range of coupling partners.

N-Phenylurea as an inexpensive and efficient ligand for Pd-catalyzed Heck and room-temperature Suzuki reactions

N-Phenylurea was found to constitute a highly efficient, yet low-priced, phosphine-free ligand for the Pd-catalyzed Heck and room-temperature Suzuki reactions of aryl bromides and iodides with very high turnover numbers (ca. 103-104).