14080-18-3

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 17314-33-9 tributyltin phenyl sulfide 
• 100-58-3 phenylmagnesium bromide 
• 89283-87-4 2-thiocyanatopyrimidine 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 591-50-4 iodobenzene 
• 131242-36-9 2-sulfanylpyrimidine 
• 98-80-6 phenylboronic acid 
• 100-63-0 phenylhydrazine 
• 882-33-7 diphenyldisulfane 
• 38111-44-3 phenylzinc(II) bromide 
• 61686-49-5 2-pyrimidylsulfenyl chloride 
• 4595-60-2 2-bromopyrimidine 

Downstream Products

• 27110-82-3 2-(furan-2-yl)pyrimidine 
• 14080-17-2 2-(benzenesulfonyl)pyrimidine 
• 77232-13-4 2-p-tolyl-pyrimidine 
• 69696-00-0 2,6-Pyrimidine phenyl acetylene 
• 136-95-8 2-amino-benzthiazole 

Relevant academic research and scientific papers

Palladium catalyzed bispyrimidine thioether synthesis

The synthesis of sulfur-bridged bispyrimidines via coupling of a halopyrimidine and pyrimidine thiolate anion has been explored utilizing a palladium catalyzed cross coupling reaction. Several reaction parameters including stoichiometry and choice of solv

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

C[sbnd]S cross-coupling catalyzed by a series of easily accessible, well defined Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]

The synthesis, characterization and catalytic evaluation of a series of NHC-Ni(II) complexes 1-Ni (-Me), 2-Ni (-nBu) and 3-Ni (-Bn) bearing a phthalimide fragment and a cyclopentadienyl (Cp) ligand is reported. The complexes were evaluated in C

Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water

A series of PEG-functionalized nitrogen ligands were developed to conduct an aerobic oxidative cross-coupling reaction between alkyl- or aryl-hydrazines with thiols in water. This surfactant-type catalyst enables high efficiencies and selectivities, while tolerating a large variety of functional groups. The mother liquor is still catalytically active after five runs.

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.

Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides

The formation of aryl C?S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.

Ruthenium-Catalyzed para-Selective C?H Alkylation of Aniline Derivatives

The para-selective C?H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N?H-activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N?H metalation (as opposed to C?H metalation in meta-selective processes) and form a redox active ruthenium species, to enable site-selective radical addition at the para position.

Efficient synthesis of unsymmetrical heteroaryl thioethers and chalcogenides by alkali hydroxide-mediated SNAr reactions of heteroaryl halides and dichalcogenides

An efficient alkali hydroxide-mediated SNAr reaction of heteroaryl halides has been developed for the practical synthesis of the useful unsymmetrical heteroaryl thioethers and chalcogenides. The usually odorless, easily available, lowly toxic, and easily stored and handled diorganyl dichalcogenides can be used as safer and convenient chalcogen nucleophile precursors and diverse unsymmetrical heteroaryl chalcogenides can be obtained in good to high yields by the method.

AROMATIC SULFIDE COMPOUNDS AND METHODS AND USE THEREOF

Described herein, inter alia, are aromatic sulfide compositions and methods for treating or preventing cancer using the same.

Electrochemical intramolecular c-h amination: Synthesis of benzoxazoles and benzothiazoles

A new method for metal-free intramolecular C-H amination has been developed. Electrochemical oxidation of 2-pyrimidyloxybenzenes and 2-pyrimidylthiobenzenes, which can be easily prepared from phenols and thiophenols, respectively, followed by the treatment of the resulting pyrimidinium ions with piperidine gives 2-aminobenzoxazoles and 2-aminobenzothiazoles, respectively.