17100-44-6

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 352-13-6 4-flourophenylmagnesium bromide 
• 3851-47-6 4-bromo-4'-fluorodiphenylmethanol 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 462-06-6 fluorobenzene 
• 873-75-6 4-bromobenzenemethanol 
• 459-56-3 4-fluorobenzylic alcohol 
• 5467-74-3 4-Bromophenylboronic acid 
• 1765-93-1 4-fluoroboronic acid 
• 108-86-1 bromobenzene 
• 589-17-3 p-bromobenzyl chloride 

Downstream Products

• 202716-26-5 N-benzyl-4-[4-(4-fluorobenzyl)phenyl]-4-piperidinol 
• 2069-41-2 (4-bromophenyl)-(4-fluorophenyl)methanone 
• 764708-67-0 C₁₅H₁₃F 
• 1399813-86-5 (Z)-1-[4-(4-fluorobenzyl)phenyl]prop-1-ene 
• 202716-35-6 4-[4-(4-fluorobenzyl)phenyl]-4-piperidinol 
• 181207-59-0 4-[4-(4-fluorobenzyl)phenyl]piperidine 
• 181207-58-9 4-[4-(4-fluorobenzyl)phenyl]-1,2,3,6-tetrahydropyridine 
• 181207-49-8 N-tert-butoxycarbonyl-4-[4-(4-fluorobenzyl)phenyl]-4-piperidinol 

Relevant academic research and scientific papers

A novel class of Na+ and Ca2+ channel dual blockers with highly potent anti-ischemic effects

A series of novel arylpiperidines (4a-d) which have highly potent blocking effects for both neuronal Na+ and T-type Ca2+ channels with extremely low affinity for dopamine D2 receptors were synthesized. Among these compounds, 1-(2-hydroxy-3-phenoxy)propyl-4-(4-phenoxyphenyl)-piperidine hydrochloride (4c; SUN N5030) exhibited remarkable neuroprotective activity in a transient middle cerebral artery occlusion (MCAO) model.

Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes

AlSBA-15 catalysts possessing Br?nsted acid and Lewis acid-base bifunctionalities catalyze the direct arylation of benzyl alcohols to diarylmethanes with an 85% product yield through C-O bond activation. 2 and 4wt%AlSBA-15 catalysts have been synthesised by adopting a simple and efficient post-synthetic metal implantation route. The synthesised catalysts were characterized using XRD, N2 adsorption and desorption, 27Al MAS NMR, XPS, HR-TEM, NH3 and CO2-temperature-programmed desorption (TPD) and pyridine-transmission-FTIR spectroscopy techniques to confirm the existence of Br?nsted acid and Lewis acid-base bifunctionalities. Through various control experiments, it is verified that Br?nsted acid sites activate the benzyl alcohol and Lewis base sites interact with phenylboronic acid concurrently to accomplish the coupling reaction. In the recyclability study, 4wt%AlSBA-15 preserves its activity and stability up to 5 cycles. The 4wt%AlSBA-15 catalyst unlike homogeneous catalysts does not require additives, long reaction time and expensive metals.

GLYCOLATE OXIDASE INHIBITORS AND USE THEREOF

The present invention provides pyrazoles, isoxazoles, isothiazoles, thiadiazoles, and pyridazines according to Formula I as described herein, and pharmaceutically acceptable salts thereof. Pharmaceutical compositions and methods for treating primary hyperoxaluria, type I (PH) and kidney stones are also described.

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel-Crafts reactions

This manuscript describes the application of Re2O7 to the syntheses of diarylmethanes from benzylic alcohols through solvolysis followed by Friedel-Crafts alkylation. The reactions are characterized by broad substrate scope, low catalyst loadings, high chemical yields, and minimal waste generation. The intermediate perrhenate esters are superior leaving groups to chlorides and bromides in these reactions. The polarity and water sequestering capacity of hexafluoroisopropyl alcohol are critical to the success of these processes. Re2O7 is a precatalyst for HOReO3, which serves as a less costly and easily handled promoter for these reactions. Oxorhenium catalysts selectively activate alcohols in the presence of similarly substituted acetates, indicating a unique chemoselectivity and mechanism in comparison to Br?nsted acid catalysis.

Unsymmetrical diarylmethanes by ferroceniumboronic acid catalyzed direct friedel-crafts reactions with deactivated benzylic alcohols: Enhanced reactivity due to ion-pairing effects

The development of general and more atom-economical catalytic processes for Friedel-Crafts alkylations of unactivated arenes is an important objective of interest for the production of pharmaceuticals and commodity chemicals. Ferroceniumboronic acid hexafluoroantimonate salt (1) was identified as a superior air- and moisture-tolerant catalyst for direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes with stable and readily available primary and secondary benzylic alcohols. Compared to the use of classical metal-catalyzed alkylations with toxic benzylic halides, this methodology employs exceptionally mild conditions to provide a wide variety of unsymmetrical diarylmethanes and other 1,1-diarylalkane products in high yield with good to high regioselectivity. The optimal method, using the bench-stable ferroceniumboronic acid salt 1 in hexafluoroisopropanol as cosolvent, displays a broader scope compared to previously reported catalysts for similar Friedel-Crafts reactions of benzylic alcohols, including other boronic acids such as 2,3,4,5-tetrafluorophenylboronic acid. The efficacy of the new boronic acid catalyst was confirmed by its ability to activate primary benzylic alcohols functionalized with destabilizing electron-withdrawing groups like halides, carboxyesters, and nitro substituents. Arene benzylation was demonstrated on a gram scale at up to 1 M concentration with catalyst recovery. Mechanistic studies point toward the importance of the ionic nature of the catalyst and suggest that factors other than the Lewis acidity (pKa) of the boronic acid are at play. A SN1 mechanism is proposed where ion exchange within the initial boronate anion affords a more reactive carbocation paired with the non-nucleophilic hexafluoroantimonate counteranion.

Threefold and chemoselective couplings of triarylbismuths with benzylic chlorides and iodides using palladium catalysis

This paper describes the palladium-catalyzed studies on threefold coupling of triarylbismuth reagents with benzylic chlorides and iodides. The optimized protocol conditions are operationally simple, delivering threefold coupling of a variety of triarylbismuths in combination with benzylic chlorides and iodides. The two optimized protocols allowed the synthesis of a diverse range of unsymmetrical diarylmethanes in an efficient manner. As part of this study, chemoselective transformation of benzylic chlorides and iodides was also achieved. This journal is the Partner Organisations 2014.

Pd-catalyzed chemoselective threefold cross-coupling of triarylbismuths with benzylic bromides

An efficient palladium-catalyzed protocol was demonstrated for the chemoselective cross-coupling of functionalized benzylic bromides with triarylbismuth reagents. Under the established conditions, catalyzed by palladium in the presence of K3PO

Efficient synthesis of substituted styrenes and biaryls (or heteroaryls) with regioselective reactions of ortho -, meta -, and para-bromobenzyl bromide

Regio- and stereoselective reactions of ortho-, meta-, and para-bromobenzyl bromide under Stille and (or) Suzuki cross-coupling reactions are described that provided substituted styrene monomers and biaryls in two steps. By controlling the experimental conditions, the first coupling provided access to allylarene or diarylmethane intermediates, and the second reaction led to the desired styrenes and biaryls, substituted by a spacer arm in the ortho, meta or para position depending on the starting material. Georg Thieme Verlag Stuttgart · New York.

Selective double Suzuki cross-coupling reactions. Synthesis of unsymmetrical diaryl (or heteroaryl) methanes

Using a double Suzuki cross-coupling reaction ortho- or para-bromobenzyl bromides are easily transformed into unsymmetrical diaryl (or heteroaryl) methanes.