33777-85-4

Upstream product

• 928-49-4 hex-3-yne 
• 1194-02-1 4-fluorobenzonitrile 
• 2402-78-0 2,6-dichloropyridine 
• 1765-93-1 4-fluoroboronic acid 
• 16883-69-5 N-phenacylpyridinium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 626-05-1 2,6-Dibromopyridine 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 56-40-6 glycine 
• 544-13-8 Glutaronitrile 
• 98-98-6 2-Picolinic acid 
• 459-22-3 4-fluorophenylacetonitrile 
• 106-96-7 propargyl bromide 

Relevant academic research and scientific papers

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

Pd-Catalyzed Decarboxylation and Dual C(sp3)-H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines

The Pd-catalyzed decarboxylation and dual C(sp3)-H bond functionalization approaches have been described for the preparation of symmetrical and unsymmetrical 2,4-diarylpyridines. The developed transformations were realized using nonactivated aromatic ketones and amino acids as C-N sources. The efficacy of the catalyst and reagent combination drives the transformation toward the formation of desired products with high yields and selectivity. The described reaction conditions have seduced the self-reaction of phenylalanine via [2 + 2 + 2] cycloaddition and minimized the formation of 3,5-phenylpyridine as a side product, whereas using glycine as a C-N source, the corresponding 2,6-diarylpyridines were formed as minor products.

Sterically hindered N-aryl/benzyl substituted piperidoimidazolin-2-ylidene palladium complexes and their catalytic activities

A series of N-aryl (2a,b) or benzyl (2c,d) substituted piperidoimidazolinium salts and their palladium complexes (3a-d) were prepared and characterized by 1H, 13C NMR, IR spectroscopy and elemental analysis. The crystal structures of 3a and 3c have been determined by X-ray crystallography. Thermogravimetric analysis (TGA) was applied to complexes (3a–d). The palladium complexes have been employed as catalyst for Suzuki-Miyaura cross coupling. The N-aryl substituted complex 3b was a highly efficient precatalyst and successfully employed in Suzuki-Miyaura cross coupling reactions of (hetero)aryl chlorides with arylboronic acids in air. In addition, the oxidative addition step of the reaction mechanism involving chlorobenzene and the catalysts 3a, 3b, 3c and 3d were computationally investigated by the DFT-ω-B97X-D method and complete agreement were obtained with the catalytic results. To measure σ-donating and π-acceptor properties of the new ligands, the rhodium carbonyl complexes were also prepared.

Method for double carbon-hydrogen activation and arylation of pyridine compounds

The invention discloses a method for double carbon-hydrogen activation and arylation of pyridine compounds, and belongs to the field of methodology of organic synthesis. The method comprises the following steps: mixing a palladium source, a phosphine ligand, a copper salt or an oxide of copper, an alkali and aryl halide, placing the mixture in a nitrogen gas environment, then adding an additive, 4-substituted pyridine and a solvent, and carrying out a heating reaction, to obtain a C2-site and C6-site double aryl substituted pyridine compounds through a carbon-hydrogen activation mechanism, wherein a substituent group of 4-substituted pyridine is any one of hydrogen, alkyl and aryl. The method has the advantages of wide application range, simple operation steps, no need of pre-activation of a pyridine ring, and no need of introduction of a guiding group, and extremely high atomic economy and practicability.

One-pot synthesis of symmetrical 2,6-diarylpyridines via palladium/copper-catalyzed sequential decarboxylative and direct C-H arylation

A palladium(II)/copper oxide (Cu2O)-catalyzed one-pot decarboxylative and direct C-H arylation of 2-picolinic acid with aryl bromides has been developed. Various aryl bromides have been shown to be efficient coupling partners in the presence of dimethyl sulfate, furnishing symmetrical 2,6-diarylpyridines 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

Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright

Highly regioselective assembly of Di- or trisubstituted pyridines from arynes, isocyanides, and 3-bromo- or 3-acetoxypropynes

A facile synthetic method for the preparation of di- and trisubstituted pyridines with high regioselectivity through an intramolecular pericyclization strategy is disclosed. The multicomponent reaction of isocyanides, arynes, and 3-bromopropyne affords disubstituted pyridines in good yields. In contrast, the use of 3-acetoxypropyne results in the formation of trisubstituted pyridines through intramolecular pericyclization of an in situ formed azatriene. In this way, desirable pyridines can be constructed in a one-pot manner. The preparation of di- or trisubstituted pyridines with high regioselectivity through the multicomponent reaction of isocyanides, arynes, and 3-bromo or 3-acetoxypropyne is described. The pyridine ring is constructed through intramolecular pericyclization of an in situ generated azatriene intermediate. The pyridine products are assembled effectively in a one-pot manner under mild conditions. Copyright

Direct ortho-arylation of N-phenacylpyridinium bromide by palladium-catalyzed C-H-bond activation

A novel palladium catalyzed direct ortho-arylation of N-phenacylpyridinium bromide was developed. The amazing N-phenacyl group regioselectively activates the C-H bond of pyridine and automatically departs from the arylated products. A kinetic isotope effe

Ni-catalyzed cross-coupling reaction of aryl chlorides with arylboronic acids in IPA without using a reducing reagent

The coupling reaction of aryl chlorides with arylboronic acids was successfully performed in isopropanol (IPA) by using [NiCl(Ph2PCH2CH2OH)2(H2O)]Cl (5), a cationic Ni(II)-complex, as a precatalyst in the absence of a reducing agent. The coupling reaction proceeded smoothly under mild conditions to provide biaryls in satisfactory to excellent yields, and formation of the undesired dechlorination products of aryl chlorides was completely prevented.