26546-24-7

Upstream product

• 13755-29-8 sodium tetrafluoroborate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 497-19-8 sodium carbonate 

Downstream Products

• 1246662-02-1 C₂₂H₂₃NO₃S 
• 1245187-58-9 C₁₇H₁₈N₂O₂ 
• 1259930-11-4 C₂₇H₃₀O₃ 
• 720-44-5 1-(4-methoxyphenyl)-1-phenylmethanol 
• 611-94-9 4-Methoxybenzophenone 
• 5739-38-8 1-(4-methoxyphenyl)-3-phenylpropan-1-one 
• 1418635-35-4 C₂₁H₁₉NO₃S 
• 1418635-16-1 C₂₁H₁₉NO₃S 
• 1365284-12-3 (R)-3-(4-methoxyphenyl)-3-phenyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide 
• 1227798-62-0 C₁₅H₂₄ClNO₂S 
• 1292307-47-1 triethylammonium tetrakis(4-methoxyphenyl)borate 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 17171-17-4 4'-methoxy-3-methylbiphenyl 

Relevant academic research and scientific papers

Iodine-catalyzed synthesis of N,N'-chelate organoboron aminoquinolate

We disclose a novel method for the synthesis of fluorescent N,N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/ R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.

Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants

Readily prepared tetraarylborates undergo selective (cross)-coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO2/O2 without any additional nitroxide-based cocatalyst. Transition-metal-free catalytic oxidative ligand cross-coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.

An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation

Conventional approaches to Pd-catalyzed alkene 1,2-carboamination rely upon the combination of a nucleophilic nitrogen-based component and an internal C-based or external oxidant. In this study, we outline an umpolung approach, which is triggered by oxidative initiation at an electrophilic N-based component and employs "standard" organometallic nucleophiles to introduce the new carbon-based fragment. Specifically, oxidative addition of a Pd(0)-catalyst into the N-O bond of O-pentafluorobenzoyl oxime esters generates imino-Pd(II) intermediates, which undergo 5-exo cyclization with sterically diverse alkenes. The resultant alkyl-Pd(II) intermediates are intercepted by organometallic nucleophiles or alcohols, under carbonylative or noncarbonylative conditions, to provide 1,2-carboamination products. This approach provides, for the first time, a unified strategy for achieving alkene 1,2-amino-acylation, -carboxylation, -arylation, -vinylation, and -alkynylation. For carbonylative processes, orchestrated protodecarboxylation of the pentafluorobenzoate leaving group underpins reaction efficiency. This process is likely a key feature in related Narasaka-Heck cyclizations and accounts for the efficacy of O-pentafluorobenzoyl oxime esters in aza-Heck reactions of this type. (Chemical Equation Presented).

Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes

Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.

Preparation of triethylammonium tetra-arylborates (TEATABs): Coupling partners for the Suzuki reaction

(Chemical Equation Presented) Six triethylammonium tetra-arylborates (TEATABs) were synthesized via a convenient reproducible procedure and characterized by spectroscopic methods (1H, 13C, 11B NMR and electrospray ionization-high-resolution mass spectrometry). The compounds could be stored at ambient temperature and were useful as reactants in the Suzuki reaction in aqueous conditions when using commercially available catalysts. Copyright Taylor & Francis Group, LLC.

Rhodium-catalyzed asymmetric arylation of N-tosyl ketimines

A rhodium-catalyzed addition of sodium tetraarylborates to N-tosyl ketimines is described. Highly efficient asymmetric catalysis has been achieved by employing a chiral diene ligand, constructing chiral amine derivatives possessing α-tetrasubstituted carbon stereocenters with high enantioselectivity.

Rhodium-catalyzed asymmetric arylation of azomethine imines

A rhodium-catalyzed addition of sodium tetraarylborates to azomethine imines has been described. Highly efficient asymmetric catalysis has also been achieved by employing a chiral diene ligand to give 1-(diarylmethyl)pyrazolidin- 3-ones with high enantioselectivity.

Ligand-free, atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature

The atom-efficient cross-coupling reaction of sodium tetraarylborates with aryl iodides and bromides was reported. The reaction can be performed directly using a catalytic system composed of palladium chloride, sodium carbonate and methanol (PdCl2/Na2CO3/MeOH) under heat-free conditions at room temperature in an open air conditions. The reactions carried out in an atom-efficient way as 4 equiv of aryl halides coupled effectively with 1 equiv of sodium tetraarylborates to furnish 4 equiv of the corresponding functionalized biaryls in good to excellent yields.