79757-92-9

Upstream product

• 106-38-7 para-bromotoluene 
• 59016-93-2 p-hydroxymethylphenylboronic acid 
• 14047-29-1 4-carboxyphenylboronic acid 
• 106-43-4 para-chlorotoluene 
• 18282-51-4 4-iodo-benzyl alcohol 
• 5142-75-6 tri(p-tolyl)bismuth 
• 1122-91-4 4-bromo-benzaldehyde 
• 5720-05-8 4-methylphenylboronic acid 
• 36393-42-7 4-(4-methylphenyl)benzaldehyde 
• 720-73-0 4'-methyl-biphenyl-4-carboxylic acid 
• 873-76-7 para-Chlorobenzyl alcohol 
• 459-56-3 4-fluorobenzylic alcohol 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 

Downstream Products

• 49743-93-3 (4'-methyl[biphenyl]-4-yl)benzo[d]oxazole 

Relevant academic research and scientific papers

Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols

An atom-efficient procedure for the synthesis of functionalized biarylmethanols via the Pd-catalyzed cross-coupling reactions of differently functionalized iodophenylmethanols and triarylbismuth reagents is described. This protecting group-free direct couplings of 2-, 3- or 4-iodophenylmethanols with triarylbismuth reagents afforded biarylmethanols in good to high yields.

Antitubercular and Antiparasitic 2-Nitroimidazopyrazinones with Improved Potency and Solubility

Following the approval of delamanid and pretomanid as new drugs to treat drug-resistant tuberculosis, there is now a renewed interest in bicyclic nitroimidazole scaffolds as a source of therapeutics against infectious diseases. We recently described a nitroimidazopyrazinone bicyclic subclass with promising antitubercular and antiparasitic activity, prompting additional efforts to generate analogs with improved solubility and enhanced potency. The key pendant aryl substituent was modified by (i) introducing polar functionality to the methylene linker, (ii) replacing the terminal phenyl group with less lipophilic heterocycles, or (iii) generating extended biaryl side chains. Improved antitubercular and antitrypanosomal activity was observed with the biaryl side chains, with most analogs achieved 2- to 175-fold higher activity than the monoaryl parent compounds, with encouraging improvements in solubility when pyridyl groups were incorporated. This study has contributed to understanding the existing structure-activity relationship (SAR) of the nitroimidazopyrazinone scaffold against a panel of disease-causing organisms to support future lead optimization.

Water-soluble palladacycles containing hydroxymethyl groups: Synthesis, crystal structures and use as catalysts for amination and Suzuki coupling of reactions

Two water-soluble monophosphine [PPh3 and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos)]-palladacycles containing hydroxymethyl groups 2-3 were prepared by cyclopalladation and chloride bridge-splitting reactions. The complexes were characterized by elemental analysis, ESI-MS and NMR. In addition, single-crystal X-ray analysis reveals that they have one-dimensional lamellar structures involving intermolecular hydrogen bonds and π-π interactions. The use of these palladacycles as catalysts for amination and Suzuki coupling of aryl chlorides in water was investigated. Complex 3 was found to be very efficient for these coupling reactions. Additionally, it was also successfully used in Suzuki coupling of (hydroxymethyl)phenylboronic acid for the synthesis of substituted 2-N-heterocyclic biarylmethanols.

Ligand-Free Pd/C-Catalyzed One-Pot, Three-Component Synthesis of Aryl-Substituted Benzimidazoles by Hydrogen-Transfer and Suzuki Reactions in Water

An efficient protocol for the ligand-free and heterogeneous Pd/C-catalyzed one-pot, three-component synthesis of aryl-substituted benzimidazoles from benzyl alcohols by using water as the solvent was developed. The reaction involves hydrogen-transfer and Suzuki reactions. This method is quite convenient and environmentally friendly.

Synthesis, biological evaluation, and 3D QSAR study of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters as N -acylethanolamine acid amidase (NAAA) inhibitors

N-(2-Oxo-3-oxetanyl)carbamic acid esters have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the

P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides

P,N,N-Pincer nickel complexes [Ni(Cl){N(2-R2PC6H 4)(2′-Me2NC6H4)}] (R = Ph, 3a; R = Pri, 3b; R = Cy, 3c) were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good functional group compatibility. the Partner Organisations 2014.

Cross-coupling of ArX with ArMgBr catalyzed by N-heterocyclic carbene-based nickel complexes

N-Heterocyclic carbene-based pincer nickel complexes were synthesized and characterized. These complexes efficiently catalyze cross-coupling of aryl Grignard reagents with aryl chlorides or fluorides under mild conditions.

Oxidative hydroxylation mediated by alkoxysulfonium ions

Oxidative hydroxylation of toluene derivatives via alkoxysulfonium ion intermediates was achieved by integration of anodic oxidation and hydrolysis to give benzyl alcohols which are also susceptible to oxidation. Alkenes were also oxidized to give 1,2-diols without overoxidation. The integration of electrochemical oxidative cyclization and hydrolysis was achieved using alkenes bearing a nitrogen atom in an appropriate position to give cyclic β-amino-substituted alcohols.

A facile one-pot preparation of potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates

Potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates have been prepared in a simple one-pot process from the corresponding hydroxy-substituted aryl halides in 51-98% yields through an in situ protection of the free hydroxyl group with τ-BuLi. Also, we successfully performed a microwave-promoted Suzuki-Miyaura cross-coupling reaction of these substrates with aryl- and alkenyl bromides in the presence of 0.5 mol % of Pd(OAc)2 catalyst without ligands.