1174895-52-3

Upstream product

• 1008-89-5 2-phenylpyridine 
• 95-49-8 2-methylchlorobenzene 
• 16419-60-6 2-Methylphenylboronic acid 
• 1236046-48-2 (2-(pyridin-2’-yl)phenyl)(o-tolyl)methanone 
• 3034-79-5 bis(2-methylbenzoyl) peroxide 

Relevant academic research and scientific papers

Pyridine-directed carbon–carbon single bond activation: Rhodium-catalyzed decarbonylation of aryl and heteroaromatic ketones

The decarbonylation of 2-pyridyl-substituted ketones via transition metal-catalyzed carbon–carbon bond activation provides ready access to a variety of biaryl compounds. The highly efficient and general method provides reliable decarbonylation of benzophenones including a range of functional groups and substitution patterns. The methodology has also proven highly efficient for heteroaromatic substrates, including those containing thiophenyl, indolyl, quinolinyl, and pyridine substitution.

Hydrophilic (ν6-Arene)-Ruthenium(II) Complexes with P-OH ligands as catalysts for the isomerization of allylbenzenes and C-H bond arylation reactions in water

Half-sandwich ruthenium(II) complexes containing ν6-coordinated 3-phenylpropanol and phosphinous-acid-type ligands, namely, [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)R2}] (R = Me (2a), Ph (2b), 4-C6H4CF3 (2c), 4-C6H4OMe (2d), OMe (2e), OEt (2f), and OPh (2g), have been synthesized in 44-88% yield by reacting [RuCl2{ν6:κ1(O)-C6H5CH2CH2CH2OH}] (1) with the appropriate pentavalent phosphorus oxide R2P(═O)H. The structure of [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)Me2}] (2a) was unequivocally confirmed by X-ray diffraction methods. Compounds 2a-g proved to be catalytically active in the isomerization of allylbenzenes into the corresponding (1-propenyl)benzene derivatives employing water as the sole reaction solvent, with [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)(OPh)2}] (2g) showing the best performance and a broad substrate scope (73-93% isolated yields with E/Z ratios around 90:10 employing 1 mol % of 2g and 3 mol % of K2CO3, and performing the catalytic reactions at 80 °C for 4-24 h). The results herein presented show for the first time the utility of phosphinous acids as auxiliary ligands for metal-catalyzed olefin isomerization processes, reactions in which a cooperative role for the P - OH unit is proposed. On the other hand, the utility of complexes 2a-g as catalysts for ortho-arylation reactions of 2-phenylpyridine in water is also briefly discussed.

Combination of RuCl3·: X H2O with PEG-a simple and recyclable catalytic system for direct arylation of heteroarenes via C-H bond activation

A simple and recyclable catalytic system for direct arylation of heteroarenes via C-H bond activation was developed with a relatively inexpensive RuCl3·xH2O as a catalyst and PEG-400 as a green medium without any additive or ligand.

Palladium(II)-catalyzed oxidative ortho -arylation of 2-phenylpyridines

A palladium(II)-catalyzed oxidative ortho-arylation of 2-phenylpyridines via direct C-H activation with aryl boric acids is described. The reaction could be conducted under mild conditions in the presence of Pd(OAc) 2/Cu(OTf)2/TBHP system, and a variety of the azacyclic compounds bearing a biaryl unit were obtained with moderate to good yields. Georg Thieme Verlag Stuttgart, New York.

Ruthenium(ii)-catalyzed selective monoarylation in water and sequential functionalisations of C-H bonds

The ruthenium(ii)-phosphine catalyst RuCl2(PPh 3)(p-cymene) operating water selectively leads to ortho monoarylation, with arylchlorides and heteroarylhalides, of functional arenes. Further catalytic heteroarylation with Ru(OAc)2(p-cymene) in water produces mixed bifunctional derivatives.

C-H bond functionalisation with [RuH(codyl)2]BF4 catalyst precursor

Direct catalytic diarylation with (hetero)arylhalides of arenes containing an heterocycle (pyridine, oxazoline, pyrazole) has been performed with a ruthenium catalyst assisted by a coordinating base. It constitutes a green process for cross-coupled C-C bo

A highly efficient ruthenium(II) catalyst with (1,2-diarylvinyl)phosphine ligands for direct ortho arylation of 2-arylpyridine with aryl chlorides

A series of (1,2-diarylvinyl)phosphine ligands were synthesized, and their ruthenium complexes have been prepared. The structure of [(1,2-diphenylvinyl) phosphine](η6-cymene)RuCl2 (C1) was confirmed by X-ray crystallography. Ruthenium (1,2-diarylvinyl)phosphine complexes are highly efficient catalysts for direct ortho arylation of 2-arylpyridine with a range of aryl chlorides (electronrich and electron-poor aromatic chlorides). Highly controllable formation of monoarylation and diarylation through functionalization of C-H bonds on the aromatic ring were achieved.

RuCi3 xH2O-catalyzed direct arylation of arenes with aryl chlorides in the presence of triphenylphosphine

A study was conducted to demonstrate the RuCl3·xH 2O catalytic system for direct arylation of arenes with aryl chlorides. The phenylation of benzo[h]quinoline with chlorobenzene was investigated under preliminary studies. The reaction of benzo[h]quinoline and chlorobenzene N-methyl-2-pyrrolidone (NMP) formed Ph as the only product in 86-93% yields at 120-130 8C in the presence of K2CO3 using 5 mol% RuCl3·xH2O and 10 mol% PPh3. It was observed that the presence of an excess of ligand did not affect formation of Ph, while sub-stoichiometric ligand amounts led to a reduced conversion for benzo[h]quinoline. The arylation and benzylation of benzo[h]quinoline with various aryl chlorides was also investigated under the study.

Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation

The ruthenium catalysed direct functionalisation of arene C-H bonds by aryl halides is reported. Reactions were performed in diethyl carbonate (DEC) instead of N-methylpyrrolidone (NMP), the solvent of choice used in most ruthenium catalysed C-H bond transformations. The use of diethyl carbonate facilitates the workup procedure thus reducing the amount of waste water. The slight loss of activity due to the use of diethyl carbonate is counterbalanced by the improvement of the catalyst efficiency achieved by a judicious choice of additives. Several arenes containing an N-heterocycle as a directing group have been diarylated. The Royal Society of Chemistry 2009.

Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.