22865-59-4

Upstream product

• 27297-82-1 4-Brom-benzolsulfonsaeure-(4-nitro-benzyl)-ester 
• 100-66-3 methoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 100-14-1 4-nitrobenzyl chloride 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 619-73-8 4-nitrobenzyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 586-78-7 para-nitrophenyl bromide 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 19824-21-6 C₁₀H₁₅N₂O₂⁽¹⁺⁾*Br^(1-) 
• 842-58-0 (4-methoxyphenyl)(4-nitrophenyl)methanol 
• 24067-17-2 4-nitrophenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1151-94-6 4-methoxy-4'-nitrobenzophenone 
• 21969-07-3 4-(4-nitrobenzyl)phenol 

Relevant academic research and scientific papers

Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst

N-heterocyclic carbene-palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C-N bond activation has been developed. Notably, in the presence of the easily prepared and bench-stable Pd-PEPPSI precatalyst, the Csp3-N bond activation of the benzylammonium salt even proceeded smoothly in isopropanol at room temperature.

Dual copper- and photoredox-catalysed C(sp2)-C(sp3) coupling

The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C-C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)-C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

Picolinamide modified β-cyclodextrin/Pd (II) complex: Asupramolecular catalyst for Suzuki-Miyaura coupling of aryl, benzyl and allyl halides with arylboronic acids in water

Novel supramolecular catalysts for Suzuki-Miyaura coupling were prepared and characterized by NMR, FT-IR, TEM, XRD, TGA, and XPS. The resulting picolinamide-modified β-cyclodextrin/Pd(II) complex (Pd(II)@PCA-β-CD) showed very efficient catalytic activity for Suzuki-Miyaura coupling of aryl, benzyl, and allyl halides with arylboronic acids in an environmentally benign aqueous solution. Various organic halides including chlorides can produce good to excellent yields with phenyl-boronic acid and a catalytic amount of Pd(II)@PCA-β-CD. This hydro-soluble catalyst was capable of being reused for at least eight runs with only a slight loss of catalytic activity. A putative mechanism of the Pd(II)/Pd(IV) catalytic cycle was also explored and calculated by ab initio QM/MM methods.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

Design, Synthesis, and Evaluation of Thyronamine Analogues as Novel Potent Mouse Trace Amine Associated Receptor 1 (m TAAR1) Agonists

Trace amine associated receptor 1 (TAAR1) is a G protein coupled receptor (GPCR) expressed in brain and periphery activated by a wide spectrum of agonists that include, but are not limited to, trace amines (TAs), amphetamine-like psychostimulants, and end

SYNTHETIC ANALOGUES OF 3-IODOTHYRONAMINE (T1AM) AND USES THEREOF

Novel synthetic analogues of 3-iodothyronamine of formula (I), pharmaceutical compositions containing the same, and medical uses thereof are described.

One-pot synthesis of symmetrical and unsymmetrical diarylmethanes via diborylmethane

A one-pot synthesis of diarylmethanes from air-stable diborylmethane via the Suzuki-Miyaura cross-coupling reaction is described. The present approach realizes the synthesis of various symmetrical and unsymmetrical diarylmethanes in good to excellent yields.

Synthesis of diarylmethane derivatives from Stille cross-coupling reactions of benzylic halides

A catalyst precursor prepared in situ from palladium acetate and a phosphine ligand was used for the Stille cross-coupling reaction of benzylic bromides and chlorides with aryltributyltin analogues. The reactions were performed at 80 °C using dppf as ligand in the presence of KF, or more conveniently using PPh3 in the absence of base, furnishing diarylmethane derivatives in high yields (86-99%). Using Pd(OAc)2/PPh3 as catalyst precursor competitive Stille and Suzuki cross-coupling reactions with benzyl chloride showed that in the absence of base or in the presence of KF the Stille product is the majority product, and only the Suzuki product was obtained in the presence of KOH as base.

Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions

A highly efficient Suzuki cross-coupling reaction between benzylic halides and aryl boronic acids using palladium chloride as catalyst in acetone:water (3:1) has been developed. High yields of products, mild reaction conditions and short reaction times in the absence of ligand are important features of this method. A highly efficient Suzuki cross-coupling reaction between benzylic halides and aryl boronic acids using palladium chloride as catalyst in acetone:water (3:1) as the solvent system has been developed. High yields of products, mild reaction conditions and short reaction times in the absence of ligand are important features of this method.