5957-99-3

Upstream product

• 626-55-1 3-Bromopyridine 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 1692-25-7 3-pyridylboronic acid 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 626-60-8 3-Chloropyridine 
• 1423-26-3 (meta-(trifluoromethyl)phenyl)boronic acid 
• 110-86-1 pyridine 
• 131086-40-3 3-(trifluoromethyl)phenyl 4-methylbenzenesulfonate 
• 16518-17-5 potassium nicotinate 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 1120-90-7 3-iodopyridine 
• 121899-80-7 tris(3-trifluoro-methylphenyl)bismuthane 
• 76053-50-4 2-chloro-5-<3-(trifluoromethyl)phenyl>pyridine 

Downstream Products

• 64321-45-5 3-(m-trifluoromethylphenyl)-piperidine 
• 108281-80-7 3-<3-(trifluoromethyl)phenyl>pyridine 1-oxide 
• 64321-51-3 3-<3-(trifluoromethyl)phenyl>-N-n-propylpiperidine 
• 108281-81-8 3-<3-(trifluoromethyl)phenyl>pyridin-2(1H)-one 

Relevant academic research and scientific papers

[2,2′-bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine

The ligand [2,2′-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.

Palladium-catalyzed decarboxylative cross-coupling of 3-pyridyl and 4-pyridyl carboxylates with aryl bromides

Decarboxylative cross-coupling of 3-pyridyl and 4-pyridyl carboxylates with aryl bromides is reported. Using a bimetallic system of Cu2O and Pd(PPh3)4, the scope of the reaction is demonstrated by the synthesis of 27 pyridine-containing biaryls in moderate to good yields.

Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i

Pd-catalyzed C3-selective arylation of pyridines with phenyl tosylates

We have discovered that phenyl tosylates can be used to arylate pyridines at the C3-position using a Pd(OAc)2-1,10-phenanthroline catalyst system. We also discovered that the reaction of 4-methylpyridine with naphthyl tosylates occurred on the methyl group instead of at the C3-position. The Royal Society of Chemistry 2013.

Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: Gram-scale synthesis of (±)-preclamol

The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)2 and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (±)-preclamol is also reported.

Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure

Suzuki-Miyaura coupling reactions of aryl and heteroaryl halides with aryl-, heteroaryl- and vinylboronic acids proceed in very good to excellent yield with the use of 2-(2′,6′-dimethoxybiphenyl) dicyclohexylphosphine, SPhos (1). This ligand confers unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, for reactions of aryl chlorides at room temperature. Additionally, structural studies of various 1·Pd complexes are presented along with computational data that help elucidate the efficacy that 1 imparts on Suzuki-Miyaura coupling processes. Moreover, a comparison of the reactions with 1 and with 2-(2′,4′,6′-triisopropylbiphenyl)diphenylphosphine (2) is presented that is informative in determining the relative importance of ligand bulk and electron-donating ability in the high activity of catalysts derived from ligands of this type. Further, when the aryl bromide becomes too hindered, an interesting C-H bond functionalization-cross-coupling sequence intervenes to provide product in high yield.

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides

Pd-catalyzed Suzuki-Miyaura reaction of aryl chlorides was accomplished through the use of an active ferrocene-based triarylphosphine ligand. This air- and moisture-stable ligand was found to be effective for the cross-coupling of aryl halides at room temperature to 115 °C.

Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane: ·1/2[PdCl(C3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl halides with a range of arylboronic acids with very high ratio substrate/catalyst in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, pyrimidines or a furane have been used successfully.

Efficient coupling of heteroaryl bromides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl bromides with arylboronic acids with a very high substrate/catalyst ratio in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, a pyrimidine or a furane have been used successfully.

N-Substituted 1,2,3,4,4a,5,6,10b-Octahydrobenzoquinolines and 3-Phenylpiperidines: Effects on Central Dopamine and ? Receptors

N-Substituted analogues of trans-7 and trans-9-hydroxy-1,2,3,4,4a,5,6,10b-octahydrobenzoquinoline (trans-7- and trans-9-OH-OHBQ) were tested for dopamine (DA) D2 receptor affinity by using in vitro spiperone and in vivo 5,6-di-n-Pr-ADTN binding ass