83135-54-0

Upstream product

• 83135-68-6 1-acetoxy-3-phenyl-1-o-tolylpropane 
• 18916-11-5 (E)-1-methyl-2-(3-phenyl-2-propen-1-yl)benzene 
• 83135-58-4 cis-3-phenyl-1-o-tolylpropene 
• 300-57-2 allylbenzene 
• 95-46-5 2-methylphenyl bromide 
• 115117-74-3 (E)-3-(2'-methylphenyl)-2-propen-1-ol acetate 
• 143-66-8 sodium tetraphenyl borate 
• 100-42-5 styrene 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 2996-92-1 phenyl trimethylsiloxane 
• 501922-06-1 (E)-3-(2-methylphenyl)-2-propenol 
• 70625-62-6 methyl (E)-3-(2-methylphenyl)-2-propenoate 
• 939-57-1 (E)-3-(2-methylphenyl)acrylic acid 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 18916-11-5 (E)-1-methyl-2-(3-phenyl-2-propen-1-yl)benzene 
• 83135-58-4 cis-3-phenyl-1-o-tolylpropene 
• 1378973-33-1 (E)-N-(1-phenyl-3-o-tolylallyl)benzenamine 
• 1378973-35-3 (E)-N-(3-phenyl-1-o-tolylallyl)benzenamine 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Csp2-Csp3Cross Coupling Using Phosphonium Salts

A nickel-catalyzed reductive cross coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles, which granted direct construction of the C(sp2)-C(sp3) bond, is successfully developed. The protocol features broad substrate scope, high-functional-group tolerance, and heterocycle compatibility. Notably, the much more challenging reductive cross coupling with heterocyclic thiazolylphosphonium salts has also been accomplished for the first time.

C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles

Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.

In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids

A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).

Synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives via direct decarboxylative coupling of α,β-unsaturated carboxylic acids with benzyl boronic acid pinacol ester

The first copper-catalyzed cross-coupling reaction between benzyl boronic acid pinacol ester and α,β-unsaturated carboxylic acids was described. The ready availability of the starting materials and excellent E selectivity make this protocol a safe and operationally convenient strategy for the efficient synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives.

Photochemical Heck benzylation of styrenes catalyzed by Na[FeCp(CO)2]

Iron-catalyzed Heck coupling of benzyl chlorides and styrenes proceeds under photochemical conditions using the well-known anionic complex, [FeCp(CO)2]- (Fp-), as a catalyst. The reaction likely proceeds through the established SN2 mechanism for Fp- alkylation, followed by styrene migratory insertion and β-hydride elimination steps that are enabled by photochemical CO dissociation.

Copper-catalyzed oxidative alkenylation of C(sp3)-H bonds via benzyl or alkyl radical addition to β-nitrostyrenes

A new method for the preparation of (E)-β-alkylstyrene derivatives has been developed via the addition of a benzyl or alkyl radical to β-nitrostyrenes using di-tert-butyl peroxide (DTBP) as the oxidant in the presence of Cu powder catalyst. The C-H bonds in various toluene derivatives, ethers, alkanes and alcohols were successfully converted into C-C bonds to yield the corresponding (E)-β-alkylstyrene derivatives in moderate to good yields.

A palladium NNC-pincer complex: An efficient catalyst for allylic arylation at parts per billion levels

Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50°C gave the corresponding arylated products in excellent yields. Total turnover numbers of up to 500 000 000 and turnover frequencies of up to 11 250 000 h-1 were achieved.

Synthesis of polysubstituted olefins by Pd-catalyzed cross-coupling reaction of tosylhydrazones and aryl nonaflates

Aryl nonaflates are employed as electrophiles in the Pd-catalyzed cross-coupling with tosylhydrazones affording di-, tri-, and tetrasubstituted olefins. Fine tunning of the reaction conditions are required to accomplish the coupling successfully, includin

Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system catalyses efficiently the Heck reaction of aryl halides with linear alkenes such as pent-1-ene, oct-1-ene or dec-1-ene. Selectivities up to 70% in favour of E-1-arylalk-1-ene isomers can be obtained. In the presence of cyclic alkenes the selectivities of the reactions strongly depends on the ring size. Addition to cyclohexene or cycloheptene led mainly to 1-arylcycloalk-3-ene derivatives. On the other hand, addition to cyclooctene led to 1-arylcycloalk-1-ene adducts.

Double-Bond-Stabilizing Abilities of 1-Methyl-2-pyrrolyl, 9-Anthryl, and o-Tolyl Substituents

Equilibrium constants have been determined for the isomerisations of trans-PhCH=CHCH2X to trans-PhCH2CH=CHX, where X is 1-methyl-2-pyrrolyl, 9-anthryl, and o-tolyl.The values (estimated standard deviations) at 30 deg C in tert-butyl alcohol are 1.53 (0.04), 0.342 (0.022), and 0.407 (0.011), respectively.The equilibrium constant for the 9-anthryl case is only about two-thirds as large as a value reported previously.Steric factors are believed to be the most important reason 9-anthryl and o-tolyl groups are poorer double-bond-stabilizing substituents than phenyl groups.Resonance effects are probably decisive in making 1-methyl-2-pyrrolyl substituents better than phenyl but not as good as 2-furyl at stabilizing double bonds.The organolithium compounds formed in the reaction of butyllithium with either trans-1-(9-anthryl)-3-phenylpropene (7) or trans-3-(9-anthryl)-1-phenylpropene (8) react with water to give about 11percent 7, 27percent 8, and 58percent of what appears to be 9-(3-phenyl-2-propenylidene)-9,10-dihydroanthracene.Similar quenching of organolithium compounds in the o-tolyl case gave approximately the equilibrium mixture and in the 1-methyl-2-pyrrolyl case gave almost equal amounts of cis-1-(1-methyl-2-pyrrolyl)-3-phenylpropene (37percent), trans-1-(1-methyl-2-pyrrolyl)-3-phenylpropene (33percent), and trans-3-(1-methyl-2-pyrrolyl)-1-phenylpropene (30percent).The equilibrium constant for the trans-to-cis isomerization of PhCH2CH=CHX at 25 deg C is 0.164 (0.011) when X is 1-methyl-2-pyrrolyl, 0.801 (0.027) when X is 9-anthryl, and 0.039 (0.011) when X is o-tolyl. trans-1-(2-Pyrrolyl)-3-(dimethylamino)propene was prepared but could not be isomerized in the presence of potassium tert-butoxide, probably because of anion formation at the pyrrole NH position.In tert-butyl alcohol-dimethyl sulfoxide containing potassium tert-butoxide, trans-1-(1-methyl-2-pyrrolyl)-3-(dimethylamino)propene appeared to isomerize to trans-3-(1-methyl-2-pyrrolyl)-1-(dimethylamino)propene with an equilibrium constant of 21 (5), but the evidence for this is incomplete.