14596-83-9

Upstream product

• 14596-82-8 bis(3-thiophenecarbonyl) peroxide 
• 872-31-1 3-Bromothiophene 
• 13939-06-5 molybdenum hexacarbonyl 
• 108-95-2 phenol 
• 1864-94-4 phenyl formate 
• 10486-61-0 3-thienyl iodide 
• 64-18-6 formic acid 
• 88-13-1 3-Thiophene carboxylic acid 
• 41507-35-1 3-thiophene carboxylic acid chloride 

Downstream Products

• 119405-65-1 tri-n-butyl(thien-3-yl)tin 
• 1015699-51-0 3-(3-(4-methoxyphenyl)propyl)thiophene 
• 1641-09-4 3-thiophenecarbonitrile 

Relevant academic research and scientific papers

PHOTOLYSES OF BIS(2-THIOPHENECARBONYL) AND BIS(3-THIOPHENECARBONYL) PEROXIDES IN BENZENE. PRODUCTION OF BIPHENYL FROM THE SOLVENT BENZENE CONTROLLED BY THE PHOTOLYSIS RATE

Direct and sensitized photolyses of bis(2-thiophenecarbonyl) (2-TPO) and bis(3-thiophenecarbonyl) peroxide (3-TPO) in benzene afforded biphenyl derived solely from the solvent among the products.The yield of biphenyl depended upon the rate with which the radical intermediates were generated from the peroxides in sufficiently high concentrations to dimerize.

Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound

Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.

Metal-Free O-Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes

The metal-free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly-polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings. (Figure presented.).

Mechanistic Insight into Weak Base-Catalyzed Generation of Carbon Monoxide from Phenyl Formate and Its Application to Catalytic Carbonylation at Room Temperature without Use of External Carbon Monoxide Gas

The mechanisms of the weak base-catalyzed generation of carbon monoxide (CO) and phenol from phenyl formate were investigated by experimental and theoretical methods. Kinetic studies revealed a first-order reaction in both phenyl formate and the base. The reaction was found to proceed by an E2 α-elimination pathway, which involves the abstraction of the formyl proton of phenyl formate, simultaneously generating CO and phenoxide. The reaction rate was affected by the substituents on phenyl formate, the polarity of solvents, and the basicity of bases. The mechanistic insight obtained from these studies permitted the chemical control of the rate of CO generation, which was the key to the development of the external CO-free Pd-catalyzed phenoxycarbonylation of haloarenes at room temperature. Because of the mild reaction conditions and wide substrate scope, this phenoxycarbonylation constitutes a general, safe, and practical method to synthesize arenecarboxylic acid esters. (Figure presented.).

Palladium-catalyzed alkoxycarbonylation of aryl halides with phenols employing formic acid as the CO source

An efficient palladium-catalyzed alkoxycarbonylation of aryl halides with phenols has been developed. Various aryl benzoates have been isolated in good to excellent yields with formic acid as the CO source. The reaction proceeds smoothly under mild conditions and good functional group tolerance was observed.

Decarbonylative C-H coupling of azoles and aryl esters: Unprecedented nickel catalysis and application to the synthesis of muscoride A

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.

Palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate

Highly efficient palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate is reported. This procedure does not use carbon monoxide and affords one-carbon-elongated carboxylic acid phenyl esters in excellent yields. The reaction proceeds smoothly under mild conditions and tolerates a wide range of functional groups including aldehyde, ether, ketone, ester, and cyano groups. Furthermore, a variety of heteroaromatic bromides can be converted to the corresponding phenyl esters in high yields.

Molybdenum hexacarbonyl mediated alkoxycarbonylation of aryl halides

Mo(CO)mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)and the procedure is simple compared to the conventional method, which uses palladium catalyst under gaseous carbon monoxide. Using this procedure, a variety of carboxylic acid esters were prepared. Georg Thieme Verlag Stuttgart ? New York.

TRICYCLIC PYRAZOLE KINASE INHIBITORS

Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.