1882-47-9

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 108-88-3 toluene 
• 5153-67-3 nitrostyrene 
• 6746-22-1 tetra(p-tolyl)tin 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 
• 15738-23-5 sodium tetrakis(4-tolyl)borate 
• 101671-00-5 (E)-2-(4-methylphenyl)-1-nitroethene 
• 1135-99-5 diphenyltin(IV) dichloride 
• 3262-89-3 triphenylboroxine 
• 5720-05-8 4-methylphenylboronic acid 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 98-80-6 phenylboronic acid 
• 595-90-4 tetraphenyltin(IV) 

Downstream Products

• 6582-13-4 2-phenyl-2-p-tolyl-ethylamine 
• 6974-49-8 phenyl(p-tolyl)acetonitrile 

Relevant academic research and scientific papers

Improved catalytic asymmetric carbon-carbon bond formation using combinations of chiral and achiral monodentate ligands

Mixtures of chiral and achiral monodentate phosphoramidite ligands lead to improved enantioselectivity in the rhodium-catalyzed boronic acid addition.

Boosting Conjugate Addition to Nitroolefins Using Lithium Tetraorganozincates: Synthetic Strategies and Structural Insights

We report the first transition metal catalyst- and ligand-free conjugate addition of lithium tetraorganozincates (R4ZnLi2) to nitroolefins. Displaying enhanced nucleophilicity combined with unique chemoselectivity and functional group tolerance, homoleptic aliphatic and aromatic R4ZnLi2 provide access to valuable nitroalkanes in up to 98 % yield under mild conditions (0 °C) and short reaction time (30 min). This is particularly remarkable when employing β-nitroacrylates and β-nitroenones, where despite the presence of other electrophilic groups, selective 1,4 addition to the C=C is preferred. Structural and spectroscopic studies confirmed the formation of tetraorganozincate species in solution, the nature of which has been a long debated issue, and allowed to unveil the key role played by donor additives on the aggregation and structure of these reagents. Thus, while chelating N,N,N’,N’-tetramethylethylenediamine (TMEDA) and (R,R)-N,N,N’,N’-tetramethyl-1,2-diaminocyclohexane (TMCDA) favour the formation of contacted-ion pair zincates, macrocyclic Lewis donor 12-crown-4 triggers an immediate disproportionation process of Et4ZnLi2 into equimolar amounts of solvent-separated Et3ZnLi and EtLi.

Synthesis of palladium nanoparticles using triazolium based ionic liquids: A reusable catalyst for addition of arylboronic acids to nitrostyrenes

Formation of stable and small-sized palladium nanoparticles of diameter 9.4 nm was accomplished by a simple heating of Pd(OAc)2 in 1-octyl-1,2,4-triazolium trifluoroacetate ionic liquid under standard atmospheric hydrogen pressure. Palladium na

A nordehydroabietyl amide-containing chiral diene for rhodium-catalysed asymmetric arylation to nitroolefins

A highly enantioselective rhodium catalysed asymmetric arylation (RCAA) of nitroolefins with arylboronic acids is presented using a newly developed, C1-symmetric, non-covalent interacted, phellandrene derived, nordehydroabietyl amide-containing chiral diene under mild conditions. Stereoelectronic effects were studied, suggesting an activation of the bound substrate through the secondary amide as a hydrogen-bond donor.

Palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrenes

A palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrene is reported. The catalytic system employing iPr-IsoQuinox as a chiral ligand in MeOH solvent under an air atmosphere provides the chiral diarylsubstituted products in high yields with good enantioselectivities. A variety of functionalized nitrostyrenes can be used, and the method tolerates some variation in arylboronic acid scope. The stereochemical outcome can be explained using a stereochemical model.

An efficient method for the synthesis of α-arylated nitroalkanes and α-arylated hydroximoyl chlorides mediated by AlCl3

Friedel-Crafts alkylation of various arenes/heteroarenes to β-nitrostyrenes mediated by aluminum chloride is described. The interesting feature of this methodology pertain the formation of different products by tuning the reaction temperature. α-Arylated

Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes

The addition of aryltrialkoxysilanes to α,β-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl3, TBAF, AcOH, and a catalytic amount of Pd(OAc)2, in CH3CN at 60 °C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl3 and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.

Palladium(II)-catalyzed Michael-type hydroarylation of nitroalkenes using aryltins and sodium tetraarylborates

A variety of aryltin compounds and sodium tetraarylborates can be employed for Michael-type hydroarylation reactions of nitroalkenes to afford β-arylnitroalkanes in moderate to good yields in the presence of either LiCl, MgCl2, or CaCl2 and a catalytic amount of palladium(II) salt (0.05 molar amount) in acetic acid. Results show that 50-70% of aryl groups out of all in these aryl compounds can be transferred to the products in this hydroarylation. The addition of a catalytic amount (0.05-0.10 molar amount) of a Lewis acid chloride, BiCl3 or SbCl3, much improves the product yield in some cases.

A novel catalytic activity of bismuth(III) salts in palladium(II)-catalyzed atom economical Michael-type hydroarylation of nitroalkenes with aryltin compounds

A novel catalytic effect of bismuth(III) salts such as BiCl3, Bi2O3, and Bi(NO3)3·5H2O has been disclosed in new palladium(II)-catalyzed Michael-type hydroarylation of nitroalkenes with aryltin compounds. The reaction is atom economical in the tin compounds and slightly fewer than four aryl groups of tetraaryltins can be transferred to the products.