613-37-6

Usage

Chemical Properties

white powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 1060, 1995 DOI: 10.1021/jo00109a044

InChI:InChI=1/C13H12O/c1-14-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 92-69-3 4-Phenylphenol 
• 132777-63-0 3-(4-methoxyphenyl)cyclohexanol 
• 17138-79-3 1-(4-methoxyphenyl)cyclohexanol 
• 51-66-1 4-methoxyacetanilide 
• 104-94-9 4-methoxy-aniline 
• 127-09-3 sodium acetate 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 64-19-7 acetic acid 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 71-43-2 benzene 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 

Downstream Products

• 36330-87-7 4-(4'-methoxy-biphenyl-4-yl)-4-oxo-butyric acid 
• 63471-87-4 4-(4-methoxy-biphenyl-3-yl)-4-oxo-butyric acid 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 15854-73-6 3-nitro-4-methoxybiphenyl 
• 58743-83-2 4-bromo-4'-methoxylbiphenyl 
• 74447-73-7 3-bromo-4-methoxybiphenyl 
• 613-36-5 4-cyclohexylanisole 
• 68294-33-7 4-(4-methoxy-phenyl)-benzophenone 
• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 94549-56-1 4-methoxy-3-(toluene-4-sulfonyl)-biphenyl 
• 103594-13-4 (1,4,4-Trimethoxy-cyclohexa-2,5-dienyl)-benzene 
• 77422-75-4 C₂₀H₁₉N₃OS 
• 92-94-4 [1,1';4',1'']terphenyl 
• 64422-96-4 trans-(4-methoxycyclohexyl)benzene 

Relevant academic research and scientific papers

Structure-activity relationship of N-heterocyclic carbene-Pd(II)-imidazole complexes in Suzuki-Miyaura coupling between 4-methoxyphenyl chloride and phenylboronic acid

A series of N-heterocyclic carbene-PdCl2-imidazole [NHC-Pd(II)-Im] complexes were synthesized and the structure of most of them was unambiguously determined by X-ray single-crystal diffraction. The structure-activity relationship of these complexes was investigated for the Suzuki-Miyaura coupling between 4-methoxyphenyl chloride and phenylboronic acid, and the effect of the NHCs and Im moieties were fully discussed. The sterically hindered IPr-based complex showed the highest catalytic activity. Copyright

Porphyrin-based polymer-supported palladium as an excellent and recyclable catalyst for Suzuki–Miyaura coupling reaction in water

A porphyrin-based polymer with high surface area was synthesized using 5,10,15,20-tetraphenylporphyrin through a one-pot Friedel–Crafts alkylation reaction. Pd(II) was successfully supported on this polymer. This strategy provides an easy approach to produce highly stable Pd–porphyrin-based polymer. The resulting Pd catalyst was characterized using Fourier transform infrared and X-ray photoelectron spectroscopies, thermogravimetric analysis, scanning and transmission electron microscopies and N2 adsorption–desorption measurements. This porphyrin-based polymer-supported Pd was used as a heterogeneous catalyst for Suzuki–Miyaura coupling reaction in water. The results demonstrated that this Pd catalyst indeed exhibited excellent catalytic activity and recycling performance in water, even for inactive aryl chloride substrate. A new heterogeneous strategy for catalyzing the Suzuki–Miyaura reaction in water is provided.

Palladium(II) Complexes with Small N-Heterocyclic Carbene Ligands as Highly Active Catalysts for the Suzuki-Miyaura Cross-Coupling Reaction

Four new palladium(II) complexes of the type [Pd(NHC)2X2] with N-heterocyclic carbene (NHC) ligands of relatively small steric hindrance were prepared and characterized by using spectroscopic and X-ray methods. For [Pd(bmim-y)2Br2] (bmim-y=1-butyl-3-methylimidazol-2-ylidene), crystals of both cis and trans isomers were obtained. All the studied complexes demonstrated very high activity in Suzuki-Miyaura cross-coupling in ethylene glycol, which yielded turnover numbers of up to 760000. High activity was also observed if NaBPh4 was used instead of PhB(OH)2, and the best results (turnover number=580000) were obtained with [Pd(emim-y)2Cl2] (emim-y=1-ethyl-3-methylimidazol-2-ylidene). In the reaction mixture, different forms containing [Pdx(NHC)y]+ fragments (x=1-4, y=2-5) were identified by using ESI-MS. In the presence of Suzuki-Miyaura reaction substrates, catalytic palladium intermediates with aryl groups-[Pd(NHC)2Ph]+ and [Pd3(NHC)4Ph]+-were detected. Additional mechanistic investigations, such as TEM observations and mercury poisoning experiments, substantiated the formation of nanoparticles as a catalyst resting state. These heterogeneous particles serve as a reservoir for soluble palladium species-atoms or clusters that function as homogeneous catalysts for the Suzuki-Miyaura reaction.

In situ prepared mesoporous silica nanosphere supported palladium(ii) 2-aminopyridine complex catalyst for Suzuki-Miyaura cross-coupling reaction in water

We report the synthesis and catalytic activities of a mesoporous silica nanosphere supported palladiumII 2-aminopyridine complex (Pd-AMP-MSN). First, chloroalkyl functionalized mesoporous silica nanospheres (Cl-MSN) is prepared by an in situ co-condensation reaction of tetraethyl orthosilicate (TEOS) with ((chloromethyl)phenylethyl)trimethoxysilane (CMPE-TMS) using cetyltrimethylammonium bromide (CTAB) as the structure directing agent. The reaction of Cl-MSN with 2-aminopyridine followed by complexation with palladium acetate produces the catalyst Pd-AMP-MSN. FTIR spectroscopic analysis confirms the presence of 2-aminopyridine functionality inside the mesopores of the Pd-AMP-MSN. Nitrogen adsorption-desorption and X-ray diffraction analyses reveal mesoporous structures of the Pd-AMP-MSN catalyst with a specific surface area of 372 m2 g-1, a pore volume of 0.172 cm3 g-1 and a narrow pore size distribution (D ～ 1.92 nm). FESEM and HRTEM results indeed show the formation of nanospheres with mesoporous structures. This catalytic system exhibits excellent activity in Suzuki-Miyaura cross-coupling reactions of aryl iodides, aryl bromides and also aryl chlorides with phenylboronic acids in water medium with high yields. This Pd-AMP-MSN catalyst could be quantitatively recovered by simple filtration and is found to be highly active without any significant loss of its catalytic activity in eight consecutive runs.

Controlled synthesis of nickel(ii) dihalides bearing two different or identical N-heterocyclic carbene ligands and the influence of carbene ligands on their structures and catalysis

Ni(ii) dihalides bearing two different or identical NHC ligands have been prepared via a controlled indene elimination synthesis, and the former product provides a new route for the design of biscarbene Ni(ii)-based catalysts. The indene elimination reaction of the indenynickel(ii) complex (1-H-Ind)Ni(NHC)X (Ind = indenyl) with one equiv. of a distinct imidazolium salt at 100 °C afforded the first example of Ni(ii) dihalides bearing two different NHC ligands, i.e., Ni(iPr)(IPr)X2 [iPr = 1,3-diisopropylimidazol-2- ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), X = Cl, 1; X = Br, 2] and Ni(iPr)(IMes)Br2 [IMes = 1,3-bis(mesityl)imidazol-2- ylidene, 3]. Alternatively, complexes 1-3 can be synthesized using a bis-indenyl Ni(ii) complex (1-H-Ind)2Ni as starting materials via a step-by-step indene elimination at different reaction temperatures. The direct reaction of (1-R-Ind)2Ni (R = H or Me) with two equiv. of imidazolium salts at 100 °C afforded Ni(ii) dihalides bearing two identical NHC ligands, i.e., Ni(iPr)X2 (X = Cl, 4; X = Br, 5) and Ni(IPr)Cl2 (6). All of these complexes were characterized by elemental analysis, NMR spectroscopy and X-ray crystallography for complexes 1-5. The two identical or different NHC ligands in complexes 1-6 changed the coordination sphere of the nickel center from a typical square-planar geometry to a slightly tetrahedral array. A preliminary catalytic study on the cross-coupling reactions of aryl Grignard reagents with aryl halides revealed that complexes 1 and 2 possess the highest activity. In comparison, complexes 3 and 6 exhibited moderate activity and the least active complexes were 4 and 5.

Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium

matrix presented We demonstrate that Pd/C without added ligands catalyzes the Suzuki cross-coupling reaction with aryl chlorides. The ability of heterogeneous Pd to activate the C-Cl bond is explained in terms of a synergistic anchimeric and electronic effect that occurs between the Pd surface and the aryl chloride. Furthermore, the importance of selectivity control following C-Cl bond activation is illustrated by the striking role that solvents play in determining homo- vs cross-coupling pathways of the aryl chlorides.

Highly active Pd nanoparticles dispersed on amine functionalized layered double hydroxide for Suzuki coupling reaction

The synthesis of well dispersed palladium nanoparticles (1-5 nm) on diamine functionalized LDH is reported. The heterogeneous catalyst displayed unprecedented activity in Suzuki coupling reaction.

Suzuki-Miyaura reaction in water, conducted by employing an amphiphilic dendritic phosphine-palladium catalyst: a positive dendritic effect on chemical yield

A series of amphiphilic dendritic ligands with a phosphine core was synthesized by use of tris(4-hydroxyphenyl)phosphine oxide and poly(benzyl ether) dendron. The corresponding phosphine-palladium core dendrimers were applied as a catalyst to an aqueous-media Suzuki-Miyaura reaction. A positive dendritic effect on chemical yields of cross-coupling products was observed.

Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

In order to explore the different mechanisms possibly occurring in the Au-catalysed cross-coupling of ArN2BF4 and ArB(OH)2 in the presence of CsF, various stoichiometric experiments were performed on gold complexes with (P,N) ligands. Employing 2-pyridylphenyl-diphenylphosphine allowed us to suggest three different mechanistic pathways, starting either with a transmetallation step, via two consecutive single electron transfers, or by implying a transmetallation between Au(i) and Au(iii) species. Moreover, when using commercially available chiral (P,N) ligands, the asymmetric formation of atropoisomeric biaryls from suitable aryldiazonium salts and arylboronic acids could be achieved with e.e. up to 26%.

Chelate Palladium(II) Complexes with Saturated N-Phosphanyl-N-Heterocyclic Carbene Ligands: Synthesis and Catalysis

N-Phosphanyl-N-heterocyclic carbenes (NHCPs) featuring a saturated imidazolin-2-ylidene or tetrahydropyrimid-2-ylidene ring have been synthesized and characterized. The free carbenes exhibit good stability and can be stored in the solid state for months at ambient temperature without decomposition. Contrary to imidazoline-based NHCPs, which decompose by ring opening, N-phosphanyltetrahydropyrimid-2-ylidenes isomerize to 2-phosphanyl tetrahydropyrimidines upon heating. The free carbenes are capable of acting as chelating ligands toward palladium(II), forming very stable mononuclear complexes that have been structurally characterized. The catalytic potential of the complexes has been preliminarily assessed in cross-coupling reactions, most notably in the Suzuki coupling of aryl chlorides, where these complexes display promising activity, and in the copper- and amine-free Sonogashira coupling of aryl bromides.