19813-76-4

Upstream product

• 123-09-1 4-chlorophenyl methyl sulfide 
• 70398-91-3 4-(Methylthio)-phenyl isopropyl sulphide 
• 882-33-7 diphenyldisulfane 
• 104-96-1 4-methylsulfanylaniline 
• 591-50-4 iodobenzene 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 74-88-4 methyl iodide 
• 624-92-0 Dimethyldisulphide 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 71-43-2 benzene 
• 104-95-0 (4-bromophenyl)thioanisole 
• 98-80-6 phenylboronic acid 
• 100-47-0 benzonitrile 

Downstream Products

• 6462-34-6 4-(methylsulfonyl)-1,1′-biphenyl 
• 19813-90-2 4-biphenylthiol 
• 17064-45-8 2-(4-biphenylyl)benzoxazole 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1942-83-2 (1,1′-biphenyl)-4-yldiphenylphosphine oxide 
• 169963-54-6 4-(morpholino)biphenyl 
• 32228-99-2 4-phenyldiphenylamine 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 100-68-5 methyl-phenyl-thioether 
• 92-52-4 biphenyl 
• 20120-35-8 4-allylbiphenyl 

Relevant academic research and scientific papers

Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight

Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.

Modification of silica using piperazine for immobilization of palladium nanoparticles: A study of its catalytic activity as an efficient heterogeneous catalyst for Heck and Suzuki reactions

An efficient heterogeneous palladium catalyst system has been developed based on immobilization of Pd nanoparticles on silica-bonded N-propylpiperazine (SBNPP) substrate. SBNPP substrate can stabilize the Pd nanoparticles effectively so that it can improve their stability against aggregation. Also, grafted piperazine species onto the silica backbone prevents the removing of Pd nanoparticles from the substrate surface. It seems that the high recyclable capability of Pd-SBNPP catalysts is resulted from these two characteristics. Transmission electron microscopy (TEM) of catalyst is shown the size of Pd nanoparticles in Pd-SBNPP average of 20 nm. Furthermore, X-ray photoelectron spectroscopy (XPS) of Pd-SBNPP is shown the presence of Pd(0) in the structure of this catalyst. Overall, TEM, XPS and XRD experiments strongly suggested that Pd nanoparticles were formed and immobilized on silica-functionalized piperazine. The catalytic activity of this catalyst was investigated in the Heck and Suzuki reactions. The catalyst could be recycled several times without appreciable loss in catalytic activity.

Photochemical arylation reactions by 4-chlorothioanisole

The photochemistry of 4-chlorothioanisole (1) was investigated in various solvents, and it was found to involve the reduction to thioanisole as the main process. This occurs by heterolytic fragmentation of the triplet state of 1 and formation of the triplet 4-thiomethoxyphenylium ion, as supported by DFT calculations. The cation is trapped by alkenes and, less efficiently, by benzene, resulting in new examples of the recently emerging arylation reactions by SN1 substitution of phenyl halides. The products from alkenes involve the phenonium ion as a further intermediate. The product distribution differs from the analogous reactions via 4-methoxyphenylium for including a larger proportion of 4-(β-substituted alkyl)- rather than 4-allylthioanisoles derivatives in alcohols, for the lower fraction of rearranged α-substituted 4-alkyl-thioanisoles and for the formation of some 4-cyclopropylthioanisole with allyltrimethylsilane. The difference is accounted for by the more developed dipolar character of the C-C cyclopropane bonds in the intermediate phenonium, as indicated by DFT calculations. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

A selective metal-halogen exchange/electrophilic quench protocol on 4,4′-dibromobiphenyl 4 that proceeds under non-cryogenic conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor.

Photoinduced nucleophilic substitution of aryl halides with potassium thioacetate - A one-pot approach to aryl methyl and diaryl sulfides

Aryl methyl sulfides and diaryl sulfides were prepared by photoinduced reactions of potassium thioacetate with aryl halides under entrainment conditions. Without isolation, the arene thiolates obtained by the aromatic substitution were quenched with methyl iodide to afford the aryl methyl sulfides in 26-59% yields in a "one-pot" procedure together with the diaryl sulfides in variable yields (3-31 %). By optimization of the reaction conditions it was possible to improve the formation of the Ar2S, going from moderate to good yields (64-83%). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Palladium chloride/tetraphenylphosphonium bromide intercalated clay: New catalyst for cross-coupling of aryl halides with arylboronic acids

A facile method for the preparation of biaryl compounds is described from readily accessible aryl halides and arylboronic acids using palladium chloride/tetraphenylphosphonium bromide intercalated clay as a new catalyst.

Reaction of Nitric Oxide with Amines

Reactions of nitric oxide (NO) with amines in organic solvents were studied using Hantzsch dihydropyridines and aromatic primary amines as substrates. Hantzsch dihydropyridines are readily oxidized by nitric oxide to give the corresponding pyridines in quantitative yields. The addition of oxygen accelerates the reaction rate considerably. On the other hand, aromatic primary amines give deaminated products by the reaction with nitric oxide only in the presence of oxygen in ethereal solvents or chloroform.

SELECTIVE MONO-ARYLATION AND -ALKYLATION OF BIS(ALKYLTHIO)BENZENES; THE IMPORTANCE OF STERIC EFFECTS IN THE NICKEL-CATALYZED CROSS-COUPLING OF ARYL ALKYL SULPHIDES WITH GRIGNARD REAGENTS

Synthetically useful procedures to effect selective conversion of C-S into C-C bonds have been developed by taking advantage of the sensitivity of reactions of Grignard reagents with aryl alkyl sulphides, catalyzed by low-valent nickel species, to steric effects.It is shown that the course of these reactions is influenced by the steric requirements of both the aryl and the alkyl moieties of the sulphides.Thus, selective mono-arylation and alkylation of easily available bis(alkylthio)benzenes can be effected in medium to high yields.This allows the introduction of two different aryl or alkyl groups into the benzene nucleus by sequential substitution of the two alkylthio functions.

SELECTIVE MONO-ARYLATION AND -ALKYLATION OF CHLOROPHENYL ALKYL SULFIDES BY NICKEL CATALYSED CROSS-COUPLING WITH GRIGNARD REAGENTS

Chlorophenyl alkyl sulfides are mono-arylated and -alkylated selectively with Grignard reagents, in the presence of Ni(PPh3)2Cl2, to give aryl- and alkyl-phenyl alkyl sulfides.