53348-90-6

Upstream product

• 98437-24-2 benzofuran-2-boronic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 271-89-6 1-benzofurane 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 

Downstream Products

• 1025874-83-2 (S)-2-{[1-(4-Benzofuran-2-yl-phenyl)-meth-(E)-ylidene]-amino}-3-phenyl-propionic acid ethyl ester 
• 57045-48-4 4-cyano-4'-(benzo[b]furan-2-yl)-stilbene 

Relevant academic research and scientific papers

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.

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.

Direct arylation of benzo[b]furan and other benzo-fused heterocycles

The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]-furan.

Pyrazole[3,4-e][1,4]thiazepin-7-one derivatives as a novel class of Farnesoid X Receptor (FXR) agonists

A virtual screening procedure was applied to the discovery of structurally diverse non-steroidal Farnesoid X Receptor (FXR) agonists. From 117 compounds selected by virtual screening, a total of 47 compounds were found to be FXR agonists, with 34 of them showing activity below a concentration of 20 μM. 1H-Pyrazole[3,4-e][1,4]thiazepin-7-one-based hit compound 7 was chosen for hit-to-lead optimization. A large number of 1H-pyrazole[3,4-e][1,4]thiazepin-7- one derivatives was designed, synthesized, and evaluated by a cell-based luciferase transactivation assay for their agonistic activity against FXR. Most of them exhibited low micromolar range of potency and very high efficacy.

Palladium/tetraphosphine catalyzed suzuki cross-coupling of heteroarylboronic acids with aryl halides

(Chemical Equation Presented) cis,cis,cis-1,2,3,4- Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H 5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- or benzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases, better results in terms of ratio substrate/catalyst were obtained for the reverse reaction using heteroaryl bromides with arylboronic acids.

Catalysis in capillaries by Pd thin films using Microwave-Assisted Continuous-flow Organic Synthesis (MACOS)

(Chemical Equation Presented) Finally ... metal in a microwave! Thin films of Pd black deposited onto the inner surface of microcapillaries are efficient for metal-catalyzed transformations under flow conditions including the Suzuki-Miyama and Heck couplings. The reaction mixture is flowed through these miniature capillaries while being microwaved, and conversion times are on the order of seconds.

Development and applications of a practical continuous flow microwave cell

A series of synthetic transformations were successfully and safely scaled up to multigram quantities using focused microwave irradiation with a continuous flow reaction cell that was developed in-house and which can be easily adapted to commercially avail

One-pot three-step solution phase syntheses of thiohydantoins using microwave heating

An efficient one-pot three-step solution phase protocol suitable for library syntheses of thiohydantoins was developed. The reactions included are in the following order, Negishi or Suzuki C-C coupling reactions, reductive amination and finally a cyclisation reaction. Protocols using a solid supported reagent and protocols suitable for combinatorial chemistry were developed, all including microwave heating.