54750-99-1

Upstream product

• 19524-06-2 4-bromopyridine hydrochloride 
• 829-85-6 diphenylphosphane 
• 54750-98-0 4-(diphenylphosphino)pyridine 
• 94-00-8 4-pyridinecarboxylic acid phenyl ester 
• 4559-70-0 Diphenylphosphine oxide 
• 110-86-1 pyridine 
• 694-59-7 pyridine N-oxide 
• 1120-87-2 4-bromopyridin 
• 15854-87-2 4-iodopyridine 

Downstream Products

• 263874-99-3 Dibutyl-[4-((1E,3E)-4-pyridin-4-yl-buta-1,3-dienyl)-phenyl]-amine 

Relevant academic research and scientific papers

Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

Pyridines undergo site selective cross-coupling with secondary phosphine chalcogenides (oxides, sulfides, and selenides) in the presence of acylphenylacetylenes under metal-free mild conditions (70-75 °C, MeCN) to afford 4-chalcogenophosphoryl pyridines in up to 71% yield. In this new type of SNHAr reaction acylacetylenes act as oxidants, being stereoselectively reduced to the corresponding olefins of the E-configuration.

Metal-free SHNcross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes

Terminal acylacetylenes, typical electron-deficient acetylenes, drive SHNcross-coupling of pyridines with secondary phosphine chalcogenides under metal-free mild conditions (20-75 °C) to afford 4-chalcogenophosphorylpyridines in up to 70% yield. The reaction proceedsvia2,4-migration of chalcogenophosphoryl groups in the intermediate 1-acylvinyl-2-phosphoryl dihydropyridines with simultaneous redox elimination of the vinyl ketone oligomers. These results are generalized in a concept of trimodal (polarization/deprotonation/oxidation) catalyst-like assistance of electron-deficient acetylenes in SHNreaction of the pyridinoid heterocycles with PH-nucleophiles, which comprises: (i) repolarization (umpolung) of the pyridine ring, (ii) deprotonation of secondary phosphine chalcogenides to generate phosphorus-centered anions and (iii) oxidation of the dihydro intermediates.

Visible-Light-Induced Nickel-Catalyzed P(O)-C(sp2) Coupling Using Thioxanthen-9-one as a Photoredox Catalysis

An efficient method has been developed for photocatalytic P(O)-C(sp2) coupling of (hetero)aryl halides with H-phosphine oxides or H-phosphites under the irradiation of visible light or sunlight. The thioxanthen-9-one/nickel dual catalysis mediates this ph

A mechanistic insight into the chemoselectivity of the reaction between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids

Reactions between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids have been implemented and studied. Pyridine and isoquinoline react with propynenitrile and phosphine oxides at room temperature according to the N-vinylation/C-phosphorylation scheme to afford (Z)-N-(2-cyano-1-phenyl)ethenyl phosphoryl-1,4-dihydropyridines or -1,2-dihydroiso quinolines. In the case of pyridine on heating (80–85 °°°C), the reaction gives 4-phosphorylpyridines (SNHAr reaction) and 3-phenyl-acrylonitrile oligomers.

Site-Selective Functionalization of Pyridinium Derivatives via Visible-Light-Driven Photocatalysis with Quinolinone

The selective installation of phosphinoyl and carbamoyl moieties on the pyridine scaffold is an important transformation in synthetic and medicinal chemistry. By employing quinolinone as an efficient organic photocatalyst, we developed a catalytic system driven by visible light that forms phosphinoyl and carbamoyl radicals, which react with various heteroarenium derivatives under mild, transition-metal-free conditions. This straightforward and environmentally friendly synthetic method represents a new approach to site-divergent pyridine functionalization that offers considerable advantages in both simplicity and efficiency. Ambient temperature is sufficient for the formation of the reactive radicals, and the site-selectivity can be switched from C2 to C4 by changing the radical coupling sources. Under standard reaction conditions, phosphinoyl radicals give access to C4 products, while carbamoyl radicals selectively give C2 products. We found that the carbamoyl radical overcomes the intrinsic preference for forming the ortho-product by allowing the oxo functionality of the carbamoyl radical to electrostatically engage the nitrogen of the pyridinium substrate, which preferentially gives the ortho-product. The phosphinoyl radical cannot engage in the same interaction, because the phosphorus is too large. This novel synthetic route tolerates a broad range of substrates and provides a convenient and powerful synthetic tool for accessing the core structures of numerous privileged scaffolds.

Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.

Synthesis and photophysical properties of Eu(III) complexes with phosphine oxide ligands including metal ions

Lanthanide (Ln3+) complexes composed of luminescent Eu3+ complex and joint metal blocks (Al3+, Zn2+ and Pd2+ complexes) are reported. The Eu3+ complexes [Eu(hfa)3- (dppy)2/