607361-16-0

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1746-23-2 4-tert-Butylstyrene 
• 637-69-4 4-Methoxystyrene 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 1366392-17-7 (E)-1-(tert-butyl)-4-(2-iodovinyl)benzene 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 104-94-9 4-methoxy-aniline 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 118578-89-5 diethyl (4-tert-butyl)benzylphosphonate 

Downstream Products

• 677353-68-3 (E)-4-tert-butyl-4'-hydroxystilbene 
• 1435912-93-8 C₁₉H₂₂O 

Relevant academic research and scientific papers

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism

The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Synthetic method of toluylene compound

The invention relates to a synthetic method of a toluylene compound. According to the reaction, aryl halide or mixed halides and alkene bromine are used as a substrate. Under the action of a catalyst, a ligand, a reducing agent and an additive, the substrate in ice-water bath is slowly heated to room temperature and a mild reaction is carried out for 8-12 h so as to obtain the toluylene compound. The method has advantages of cheap catalyst metal, mild reaction, one-step reaction, simple step, short reaction time, safe operation, high yield, etc.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Pd(II) complexes with amide-based macrocycles: Syntheses, properties and applications in cross-coupling reactions

This work shows Pd(ii) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e--donating and e--withdrawing substituents on the ligand framework. Ligands constitute a N4 square-planar cavity and optimally house the Pd(ii) ion. The solution-state structure via NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.

Mizoroki-Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions. the importance of ligand composition on the catalytic activity

Dichloro-bis(aminophosphine) complexes of palladium with the general formula [(P{(NC5H10)3-n(C6H 11)n})2Pd(Cl)2] (where n = 0-2) are easily accessible, cheap and air stable, highly active and universally applicable C-C cross-coupling catalysts, which exhibit an excellent functional group tolerance. The ligand composition of amine-substituted phosphines (controlled by the number of P-N bonds) was found to effectively determine their catalytic activity in the Heck reaction, for which nanoparticles were demonstrated to be their catalytically active form. While dichloro{bis[1, 1′,1′′-(phosphinetriyl)tripiperidine]}palladium (1), the least stable complex (towards protons) within the series of [(P{(NC5H 10)3-n(C6H11)n}) 2Pd(Cl)2] (where n = 0-3), is a highly active Heck catalyst at 100 °C and, hence, a rare example of an effective and versatile Heck catalyst that efficiently operates under mild reaction conditions (100 °C or below), a significant successive drop in activity was noticed for dichloro-bis(1,1′-(cyclohexylphosphinediyl)dipiperidine)palladium (2, with n = 1), dichloro-bis(1-(dicyclohexylphosphinyl)piperidine)palladium (3, with n = 2) and dichloro-bis(tricyclohexylphosphine)palladium (4, with n = 3), of which the latter is essentially inactive (at least under the reaction conditions applied). This trend was explained by the successively increasing complex stability and its ensuing retarding effect on the (water-induced) generation of palladium nanoparticles thereof. This interpretation was experimentally confirmed (initial reductions of 1-4 into palladium(0) complexes of the type [Pd(P{(NC5H10)3-n(C6H 11)n})2] (where n = 0-3) were excluded to be the reason for the activity difference observed as well as molecular (Pd 0/PdII) mechanisms were excluded to be operative) and thus demonstrates that the catalytic activity of dichloro-bis(aminophosphine) complexes of palladium can-in reactions where nanoparticles are involved-effectively be controlled by the number of P-N bonds in the ligand system.

Size controlled synthesis of Pd nanoparticles in water and their catalytic application in C-C coupling reactions

Catalytically active Pd nanoparticles have been synthesized in water by a novel reduction of Pd(II) with a Fischer carbene complex where polyethylene glycol (PEG) was used as stabilizer. PEG molecules wrap around the nanoparticles to impart stability and prevent agglomeration, yet leave enough surface area available on the nanoparticle for catalytic activity. Our method is superior to others in terms of rapid generation and stabilization of Pd nanoparticles in water with a cheap, readily available PEG stabilizer. The size of the nanoparticles generated can be controlled by the concentration of PEG in water medium. The size decreased with the increase in the PEG: Pd ratio. This aqueous nano-sized Pd is a highly efficient catalyst for Suzuki, Heck, Sonogashira, and Stille reaction. Water is used as the only solvent for the coupling reactions.

Cyclodextrin complexation of a stilbene and the self-assembly of a simple molecular device

(E)-4-tert-Butyl-4′-oxystilbene, 1-, is thermally stable as the (E)-1- isomer but may be photoisomerized to the (Z)-1- isomer as shown by UV-vis and 1H NMR studies in aqueous solution. When (E)-1- is complexed by αCD two inclusion isomers (includomers) form in which αCD assumes either of the two possible orientations about the axis of (E)-1- in αCD·(E)-1- for which 1H NMR studies yield the parameters: k1(298 K) = 12.3 ± 0.6 s-1, ΔH1? = 94.3 ± 4.7 kJ mol-1, ΔS1? = 92.0 ± 5.0 J K-1 mol-1, and k2(298 K) = 10.7 ± 0.5 s-1, ΔH2? = 93.1 ± 4.7 kJ mol-1, ΔS2? = 87.3 ± 5.0 J K-1 mol-1 for the minor and major includomers, respectively. The βCD·(E)-1- complex either forms a single includomer or its includomers interchange at the fast exchange limit of the 1H NMR timescale. Complexation of 1- by N-(6A-deoxy-α-cyclodextrin-6A-yl)-N′- (6A-deoxy-β-cyclodextrin-6A-yl) urea, 2, results in the binary complexes 2·(E)-1- in which both CD component annuli are occupied by (E)-1- and which exists exclusively in darkness and 2·(Z)-1- in which only one CD component is occupied by (Z)-1- and exists exclusively in daylight at λ ≥ 300 nm. Irradiation of solutions of the binary complexes at 300 and 355 nm results in photostationary states dominated by 2·(E)-1- and 2·(Z)-1-, respectively. In the presence of 4-methylbenzoate, 4-, 2·(Z)-1- forms the ternary complex 2·(Z)-1-·4- where 4- occupies the second CD annulus. Interconversion occurs between 2·(Z)-1-·4- and 2·(E)-1- + 4- under the same conditions as for the binary complexes alone. Similar interactions occur in the presence of 4-methylphenolate and 4-methylphenylsulfonate. The two isomers of each of these systems represent different states of a molecular device, as do the analogous binary complexes of N,N-bis(6A-deoxy-β-cyclodextrin-6A-yl)urea, 3,3·(E)-1- and 3·(Z)-1-, where the latter also forms a ternary complex with 4-.

Ligand-free heck reaction: Pd(OAc)2 as an active catalyst revisited

Palladium acetate was shown to be an extremely active catalyst for the Heck reaction of aryl bromides. Both the base and the solvent were found to have a fundamental influence on the efficiency of the reaction, with K 3PO4 and N,N-di