147424-62-2

Upstream product

• 576-22-7 2-Bromo-m-xylene 
• 13922-41-3 1-Naphthylboronic acid 
• 86-57-7 1-Nitronaphthalene 
• 100379-00-8 2,6-dimethylbenzene boronic acid 
• 1144-13-4 naphthalen-1-yl N,N-dimethylsulfamate 
• 608-28-6 2,6-dimethyliodobenzene 
• 22871-77-8 5,5-dimethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborinane 
• 90-13-1 1-Chloronaphthalene 
• 21450-64-6 (2,6-dimethylphenyl)magnesium bromide 
• 703-55-9 1-naphthylmagnesiumbromide 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 6301-54-8 2-(naphthalen-1-yl)propan-2-ol 
• 90-11-9 1-Bromonaphthalene 
• 63509-96-6 2,6-xylyllithium 

Downstream Products

• 662143-35-3 1,3-bis(bromomethyl)-2-(1-naphthyl)benzene 
• 662143-38-6 1,3-bis(mercaptomethyl)-2-(1-naphthyl)benzene 

Relevant academic research and scientific papers

General and efficient methodology for the Suzuki-Miyaura reaction in technical grade 2-propanol

The reaction profile of a series of palladium-based catalysts was examined in the Suzuki-Miyaura reaction using technical grade 2-propanol as solvent and potassium t-butoxide as base. The results generally show high activity. The method allows for the coupling of electron-rich aryl chlorides with sterically hindered aryl boronic acids to produce tri-ortho-substituted biaryls in high yields using very mild conditions and short reaction times.

Biphenylene-substituted ruthenocenylphosphine for Suzuki-Miyaura coupling of sterically hindered aryl bromides

(Chemical Equation Presented) A highly general, active, and stable catalytic system was realized in the palladium-catalyzed Suzuki-Miyaura reactions of sterically hindered aryl bromides with arylboronic acids using biphenylene-substituted di-tert-butylrut

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, aC36H12 open geodesic polyarene

Circumtrindene (6, C, one of the largest open geodesic polyarenes ever reported, exhibits fullerene-like reactivity at its interior carbon atoms, whereas its edge carbons react like those of planar polycyclic aromatic hydrocarbons (PAHs). The Bingel-Hirsc

Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions

Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.

Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications

Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.

Non-c2-symmetric bis-benzimidazolium salt applied in the synthesis of sterically hindered biaryls

A novel non-C2-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp2 )–C(sp2 ) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls.

A substituted tricyclohexylphosphane with “conformational lock”

A substituted tricyclohexylphosphane with “conformational lock”, tri(4-trans-(tert-butyl)cyclohexyl)phosphane L, has been designed and synthesized. The ligand has shown similar steric bulkiness and conformations to tricyclohexylphosphane at solid state. The comparable or slightly better performance of ligand L compared to PCy3 in Suzuki-Miyaura coupling has demonstrated the similar steric properties of two ligands in reaction and the effectiveness of the chair conformer of the cyclohexyl rings. The ineffectiveness of both L and PCy3 in palladium-catalyzed aminations has also manifested the weakness of such ligands and a sterically more bulky ligand is needed in order to develop a more efficient amination.

Catalyst shuttling enabled by a thermoresponsive polymeric ligand: Facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium

A polymeric monophosphine ligand WePhos has been synthesized and complexed with palladium(ii) acetate [Pd(OAc)2] to generate a thermoresponsive pre-catalyst that can shuttle between water and organic phases, with the change being regulated by temperature. The structure of the polymeric ligand was confirmed with matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectrometry and size-exclusion chromatography (SEC) analysis, as well as nuclear magnetic resonance (NMR) measurements. This polymeric metal complex enables highly efficient Pd-catalyzed cross-couplings and tandem reactions using 50 to 500 ppm palladium, and this can facilitate reactions that are tolerant to a broad spectrum of (hetero)aryl substrates and functional groups, as demonstrated with 73 examples with up to 99% isolated yields. Notably, 97% Pd remained in the aqueous phase after 10 runs of catalyst recycling experiments, as determined via inductively coupled plasma-atomic emission spectrometry (ICP-AES) measurements, indicating highly efficient catalyst transfer. Furthermore, a continuous catalyst recycling approach has been successfully developed based on flow chemistry in combination with the catalyst shuttling behavior, allowing Suzuki-Miyaura couplings to be conducted at gram-scales with as little as 10 ppm Pd loading. Given the significance of transition-metal catalyzed cross-coupling and increasing interest in sustainable chemistry, this work is an important step towards the development of a responsive catalyst, in addition to having high activity, by tuning the structures of the ligands using polymer science.

Hydroxyl-functionalized triazolylidene-based PEPPSI complexes: Metallacycle formation effect on the Suzuki coupling reaction

We report the preparation and full characterization of a series of hydroxyl functionalized 1,2,3-triazolylidene-based PEPPSI complexes 2a-c and their catalytic application in the Suzuki cross coupling reaction of aryl chlorides/amides with boronic acids. Under basic reaction conditions, complexes 2a-c show a notable increase in their catalytic efficiency compared with two ether-wingtip functionalized PEPPSI analogues (3 and 4) and a commercially available NHC-Pd complex (5). The catalytic results suggest that deprotonation of the hydroxyl group in complexes 2a-c plays an important role in the overall process. Deprotonation of the alcohol moiety of complexes 2a-b with sodium tert-butoxide allows for the isolation of metallacycles 6a-b, which are proposed as the active species of cross coupling reactions.

METHOD FOR PRODUCING AROMATIC COMPOUND

In a cross coupling reaction, in a case where a halogen atom is selected as the leaving group of the raw material compound, a harmful halogen waste forms as a by-product after the reaction, and disposal of the waste liquid is complicated and environmental burden is high. In a carbon-hydrogen activation cross coupling reaction which requires no halogen atom as the leaving group, although no halogen waste forms as a by-product, the reaction substrate is considerably restricted, and the reaction remains a limited molecular construction method. A method for producing an aromatic compound, which comprises subjecting an aromatic nitro compound and a boronic acid compound to a cross coupling reaction in the presence of a metal catalyst.