92724-29-3

Upstream product

• 110252-67-0 2-(2-methoxy-phenyl)-3-oxo-3-m-tolyl-propionitrile 
• 1060684-36-7 2-(m-tolylethynyl)-O-triisopropylsilylphenol 
• 533-58-4 2-Iodophenol 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 98437-24-2 benzofuran-2-boronic acid 
• 625-95-6 3-Iodotoluene 
• 100-80-1 3-methylstyrene 
• 1380755-64-5 (E)-2-(3-methylstyryl)phenol 
• 15898-38-1 sodium 3-methylbenzenesulfinate 
• 91703-34-3 2-(β,β-dibromovinyl)phenol 
• 95-56-7 2-hydroxybromobenzene 
• 95-57-8 2-monochlorophenol 
• 1620889-14-6 C₁₇H₁₆O₂ 
• 80778-47-8 1-iodo-2-methoxymethoxybenzene 

Relevant academic research and scientific papers

Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate

A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.

One-pot Tandem Heck alkynylation/cyclization reactions catalyzed by Bis(Pyrrolyl)pyridine based palladium pincer complexes

Ligand assisted palladium catalyzed one-pot tandem Heck alkynylation/cyclization reactions for the synthesis of benzofurans was reported in this paper. Well-defined palladium-pincer complexes exhibited excellent catalytic activities for the one-pot tandem Heck alkynylation/cyclization reactions yielding benzofuran derivatives using 0.1 molpercent catalyst. All the catalytic reactions are performed in air. The effects of variables such as solvents, the temperature on the catalytic activity are also reported. High product conversion was obtained for differently substituted 2-iodophenol at 120 °C in 10 h.

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole

Well-defined and air-stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis-N-heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2-iodophenol with a variety of terminal alkynes and C-H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air-stable palladium-NHC complexes were characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis-N-heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2-iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C-H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co-catalyst.

Synthesis of benzofurans from terminal alkynes and iodophenols catalyzed by recyclable palladium nanoparticles supported on N,O-dual doped hierarchical porous carbon under copper- and ligand-free conditions

We herein report that a stable and recyclable heterogeneous catalyst, consisting of Pd nanoparticles supported on N,O-dual doped hierarchical porous carbon derived from naturally available and renewable biomass-bamboo shoots, which allows for highly efficient one-pot tandem reaction of o-iodophenols with terminal alkynes to synthesize biologically active 2-benzofuran derivatives under copper- and ligand-free conditions. The catalyst performed superior catalytic performance compared with the analogous Pd/C and supported on other metal oxides under otherwise identical conditions. A broad set of aryl and alkyl terminal alkynes can be effectively coupled /cyclized with various o-iodophenols to afford their corresponding 2-benzofurans in good to high yields with good tolerance of multiple functional groups. Moreover, the catalyst showed good stability and could be reused several times without significant loss of activity.

CuI catalyzed domino coupling–cyclization of 2-iodo-phenols and 1-alkynes to the synthesis of 2-substituted benzo[b]furans/furo-pyridines

CuI/proline-catalyzed coupling reaction of 2-iodo-phenols with terminal alkynes and the following cyclization process is carried out successively in DMSO at 80 °C. Under this tandem process, 2-substituted benzo[b]furans/furo-pyridines were synthesized in good to excellent yields with a great diversity.

Method for synthesizing benzofuran derivatives by copper-free ligand-free palladium catalyst

The invention relates to a synthesis method of benzofuran derivatives, in particular to a method for synthesizing the benzofuran derivatives by a copper-free ligand-free palladium catalyst. In the presence of K3PO4 solid and a DMF solvent, a compound 1 an

Arylation synthesis method for novel five-membered aromatic heterocycle and aromatic-ring five-membered aromatic heterocycle

The invention belongs to the technical field of organic synthesis and in particular relates to an arylation synthesis method for a five-membered aromatic heterocycle or an aromatic-ring five-memberedaromatic heterocycle under the participation of an arylhydrazine derivative serving as a novel arylation reagent. The method comprises the steps: adding a raw material and aroyl hydrazine into a reactor, and carrying out a reaction at 60-100 DEG C for 8-24h under the condition that an oxidant and a transition metal catalyst are added; after the reaction is ended, carrying out suction filtration, extracting a filtrate by using ethyl acetate, carrying out drying to obtain a crude product of a target compound, and carrying out column chromatography on silica gel to obtain a pure product of the target compound. The arylation synthesis method for the five-membered aromatic heterocycle or the aromatic-ring five-membered aromatic heterocycle is scientific and reasonable and has the advantages such as simplicity and convenience in operation, relatively high yield and simplicity in amplification and purification.

Method for synthesizing benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation

The invention discloses a method for synthesizing a benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation; a catalytic amount of catalyst nickel chloride, ligand 1,10-phenanthroline(1,10-Phen), auxiliary catalyst po

Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines

A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.