2039-69-2

Upstream product

• 3218-36-8 4-Phenylbenzaldehyde 
• 126472-66-0 (benzyl)(phenyl)phosphinic fluoride 
• 56181-61-4 4-(1-bromo-2-phenylethyl)-1,1'-biphenyl 
• 31233-64-4 1-biphenyl-4-yl-2-phenyl-ethanol 
• 1657-49-4 1-chloro-4-styrylbenzene 
• 100-59-4 phenylmagnesium chloride 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 1591-31-7 4-iodo-biphenyl 
• 4714-24-3 1-bromo-4-styrylbenzene 
• 92-52-4 biphenyl 
• 637-87-6 1-Chloro-4-iodobenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 14310-35-1 4-phenethyl-1,1′-biphenyl 

Relevant academic research and scientific papers

Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions

Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Chemoselective Hydrogenation of Alkynes to (Z) -Alkenes Using an Air-Stable Base Metal Catalyst

A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperativity.

Methanol as the Hydrogen Source in the Selective Transfer Hydrogenation of Alkynes Enabled by a Manganese Pincer Complex

The first base metal-catalyzed transfer hydrogenation of alkynes with methanol is described. An air and moisture stable manganese pincer complex catalyzes the reduction of a variety of different alkynes to the corresponding (Z)-olefins in high yields. The

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

Pd(II)-NHDC-Functionalized UiO-67 Type MOF for Catalyzing Heck Cross-Coupling and Intermolecular Benzyne-Benzyne-Alkene Insertion Reactions

A novel palladium N-heterocyclic bis-carbene dicarboxylate ligand (Pd-NHDC-H2L) was successfully synthesized. In addition, an Pd-NHDC-containing UiO-67 type MOF (UiO-67-Pd-NHDC) was prepared on the basis of a size-matched ligand mixture of biphenyl-4,4′-dicarboxylic acid/Pd-NHDC-H2L (9/1) and ZrCl4 under solvothermal conditions. The obtained UiO-67-Pd-NHC MOF can be a highly heterogeneous catalyst to promote Heck cross-coupling and intermolecular benzyne-benzyne-alkene insertion reactions.

Collaboration of Ni, polyoxometalates and layered double hydroxides: synthesis, characterization, electrochemical and mechanism investigations as nano-catalyst in the Heck coupling reaction

Nickel (Ni) nanoparticles were immobilized on the surface of magnetic MgAl layered double hydroxide intercalated 10-molybdo-2-vanadophosphate (Fe–MgAl/Mo10V2–Ni) for the first time. The presence of Ni nanoparticles onthe high-surface area Fe–MgAl LDH structure in the presence of Mo10V2 makes this catalyst an ideal option in terms of efficiency and selectivity for Heck coupling reaction. Synergic effects of Mo10V2 and Ni were investigated by an electrochemical technique. Increasing of the ECSA of the catalyst compared to Fe–Mg–Al–Ni leads to enhancement of the catalytic activity and proves the synergic effect. A new catalytic mechanism was introduced for this kind of reaction. The resulting structure and its catalytic behavior were characterized by FT-IR, XRD, ICP-AES, TEM, SEM, EDX, EBSD, XPS, BET, VSM, CV, LSV and zeta potential analyses. More importantly, Fe–MgAl/Mo10V2–Ni can easily be separated from the reaction mixture using an external magnet and reused for at least four successive runs without any substantial reduction in its catalytic activity.

Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-Defined Manganese(II) Complex

Herein we report unprecedented manganese-catalyzed semihydrogenation of internal alkynes to (Z)-alkenes using ammonia borane as a hydrogen donor. The reaction is catalyzed by a pincer complex of the earth-abundant manganese(II) salt in the absence of any

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Electrochemical Evaluation of Catalytic Activity of Various Types of LDH/Mo10V2-Pd: Application of FeNi/Mo10V2-Pd as an Efficient and Reusable Nano Catalyst in the Heck Coupling Reactions

Palladium nano particles deposited on various forms of layered double hydroxide intercalated 10-molybdovanado phosphate (M(III)M(II)/Mo10V2-Pd) were synthesized. Their electrocatalytic behavior and collaboration of all components of synthesized catalysts were evaluated in Heck coupling reaction. According to the obtained results from electrochemical and catalytic investigations, FeNi/Mo10V2-Pd was chosen as the best in term of productivity. The structural features of FeNi/Mo10V2-Pd were characterized by SEM, EDX, TEM, FT-IR, XRD, ICP-AES, LSV, chronoamperometry and CV analyses. The presence of Mo10V2 improved the catalytic activity of FeNi-Pd in the Heck coupling reaction. Also collaboration of Pd and Mo10V2 with FeNi LDH as a support was studied. This reusable solid catalyst exhibited excellent activity and the methodology is applicable to diverse substrates providing good to excellent yields of desired products. This method has advantages of high yields, low reaction times, elimination of ligand and base, heterogeneous reusable catalysts and simple methodology.