36078-99-6

Upstream product

• 696-62-8 para-iodoanisole 
• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 
• 619-44-3 methyl 4-iodobenzoate 
• 81787-63-5 2-(2-(trimethylsilyl)ethynyl)phenyl acetate 
• 67-56-1 methanol 
• 98437-24-2 benzofuran-2-boronic acid 
• 619-58-9 4-iodobenzoic acid 
• 533-58-4 2-Iodophenol 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 271-89-6 1-benzofurane 
• 19183-08-5 4-(methoxycarbonyl)benzenediazonium chloride 
• 1416276-96-4 bis[4-(methoxycarbonyl)phenyl]iodonium trifluoromethanesulfonate 
• 74733-31-6 methyl 4-(1-(hydroxyimino)ethyl)benzoate 
• 619-42-1 4-methoxycarbonylphenyl bromide 

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.

Room Temperature C-H Arylation of Benzofurans by Aryl Iodides

A robust method of room temperature direct arylation for benzofuran is reported. This discovery allows for mild arylation by commercially available aryl iodides with complete C-2 regioselectivity and tolerates a range of functional groups, including heat sensitive groups. Mechanistically, a Heck-type oxyarylation product from a direct arylation process is reported as a key piece of evidence for a carbopalladation intermediate.

New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer

The scope of photosensitizer-free visible light-driven gold-catalyzed cross-coupling was evaluated by a wide variety of organoboron and organosilicon species using four equivalents of aryldiazonium salts and (4-CF3-C6H4)3PAuCl in MeOH. In addition, a C(sp or sp2)-C(sp2) cross-coupling of organotrimethylsilanes and aryldiazonium salts was investigated. The reactions can be conducted under very mild reaction conditions, with a reduced amount of aryldiazonium salt (1.2 equiv.) by using a catalytic amount of Ph3PAuNTf2 in MeCN under irradiation with blue LEDs at room temperature.

Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam

Herein, we report on the utilization of a heterogeneous catalyst, consisting of Pd nanoparticles supported on a siliceous mesocellular foam (Pd0-AmP-MCF), for the synthesis of heterocycles. Reaction of o-iodophenols and protected o-iodoanilines with acetylenes in the presence of a Pd nanocatalyst produced 2-substituted benzofurans and indoles, respectively. In general, the catalytic protocol afforded the desired products in good to excellent yields under mild reaction conditions without the addition of ligands. Moreover, the structure of the reported Pd nanocatalyst was further elucidated with extended X-ray absorption fine-structure spectroscopy, and it was proven that the catalyst could be recycled multiple times without significant loss of activity.

Palladacycles derived from arylphosphinamides for mild Suzuki-Miyaura cross-couplings

We present a type of palladacyclic complexes derived from arylphosphinamides which can be used as efficient and versatile precatalysts for mild Suzuki-Miyaura cross-coupling. With the presence of 1.0 mol% of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be very easily prepared through a two-step procedure from the readily affordable diphenyl-phosphinic chloride and exhibit excellent stability toward air and moisture. Due to these prominent properties, the new palladacycles would find practical use in Suzuki-Miyaura couplings.

Palladium-catalyzed phosphine-free direct C-H arylation of benzothiophenes and benzofurans involving MIDA boronates

With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C-H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30-50 °C in moderate to excellent yields. MIDA boronates were used in C-H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the β-arylbenzothiophenes, and the benzofurans gave only α-aryl-substituted products.

Fluorination of 2-substituted benzo[b]furans with Selectfluor

An efficient protocol was developed to access 3-fluoro-2-hydroxy-2-substituted benzo[b]furans with Selectfluor as the fluorinating reagent in MeCN and water. By utilizing SOCl2/Py as the dehydrating agent, the compounds above were readily conve

One-Pot preparation of 2-arylbenzofurans from oximes with diaryliodonium triflate

A variety of 2-arylbenzofurans were obtained in good yields by the O-arylation of oximes with diaryliodonium triflates, followed by the treatment with HCl in dioxane under warming conditions through the [3,3]-sigmatropic reaction. The present reaction is one-pot transition metal-free method for the preparation of various 2-arylbenzofurans from oximes, which are easily available from the reaction of alkyl aryl ketones with hydroxylamine.

Room-temperature arylation of arenes and heteroarenes with diaryliodonium salts by photoredox catalysis

Aryl radicals produced by irradiation of diaryliodonium salts with visible light under the catalysis of [Ru(bpy)3]2+ undergo coupling with a wide range of arenes and heteroarenes, affording various biaryls through direct C-H arylation at room temperature. Georg Thieme Verlag Stuttgart · New York.

Radical arylation of phenols, phenyl ethers, and furans

Radical arylations of parasubstituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titaniumACHTUNGTRENUNG(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access todiversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxyl groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a b-secretase inhibitor and the synthesis of a calciumchannel modulator