75907-52-7

Upstream product

• 4919-96-4 1-phenylnaphthalen-2-ol 
• 77-78-1 dimethyl sulfate 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 17212-97-4 2-(2-methoxynaphth-1-yl)-2-propanol 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 75917-07-6 1,4-dichloro-[2]naphthol 
• 75907-53-8 4-chloro-1-phenyl-2-naphthol 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 93-04-9 2-Methoxynaphthalene 

Downstream Products

• 1416339-70-2 2-(4-methylphenyl)-1-phenylnaphthalene 
• 4919-96-4 1-phenylnaphthalen-2-ol 

Relevant academic research and scientific papers

Dimenthylphosphine P-Oxide as a Synthetic Platform for Bulky and Chiral Ligands with Dimenthylphosphino Donor Groups

Attaching di(1R)-menthylphosphino fragments (menthyl = Men = 1R,2S,5R-2-isopropyl-5-methylcyclohex-1-yl) to molecular scaffolds turns them into homochiral, bulky, electron-rich phosphine ligands with proven and potential applications in coordination chemistry and transition-metal catalysis. Dimenthylphosphine P-oxide (Men2POH; 1) is established as a platform chemical toward dimenthylphosphino-containing targets via transformation to the known ligand precursors dimenthylchlorophosphine (4) and dimenthylphosphine (6). Transformations of 1 to dimenthylphosphinyl chloride (5) and dimenthylphosphinic acid (8) are elaborated. A phospha-Michael type 1,4-addition of 1 to p-benzo-or 1,4-naphthoquinone gives the corresponding o-hydroxyaryl(dimenthyl)phosphine oxides. Deprotonation of 1 with n-BuLi provides a phosphinyl nucleophile, whose reactions with alkyl halides or 1,n-dihaloalkanes provide tertiary alkyl dimenthylphosphine oxides or 1,n-bis(dimenthylphosphino)alkane bis(P-oxides) 10a-c, respectively. As an example, oxide 10b was deoxygenated to the diphosphine Men2P(CH2)3PMen2 (11) and characterized via the square-planar complex [(Men2P(CH2)3PMen2)PdCl2] (12). A selection of P-aryl dimenthylphosphines, including PhP(Men)2 (19) and 2-ClC6H4P(Men)2 (22), as well as the menthyl analogues Men-JohnPhos (21) and Men-SPhos (24), of the respective Buchwald ligands have been prepared. The combination of the secondary phosphine oxide (SPO) 1 with PdCl2 produces halide-bridged [(Men2POH)2Pd2Cl2] (25), mononuclear [(Men2POH)2PdCl2] (26), or the halide-bridged pseudochelate complex [(Men2PO···H···OPMen2)2Pd2Cl2] (27), depending on the reaction stoichiometry and conditions, all of which have been crystallographically characterized. The new ligands 1, 19, 21, 22, and 24 and complexes 25 and 26 have been evaluated in model palladium-catalyzed C-C-and C-N-fragment coupling reactions and found to display specific reactivity profiles due to the presence of the menthyl groups. Ligand 22 in particular catalyzed an asymmetric biaryl-forming coupling to give 2-methoxy-1,1′-binaphthalene with an er of up to 93:7.

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Pyridine-based hypercrosslinked polymers as support materials for palladium photocatalysts and their application in Suzuki-Miyaura coupling reactions

A series of hypercrosslinked polymers (P1 to P8) was synthesized from pyridine and conjugated monomers to support palladium for photocatalytic Suzuki-Miyaura coupling reactions. The results of SEM, TEM and XRD analyses reveal that the supports possess a loose porous amorphous lamellar structure, and the TGA test shows that they are thermally stable. Among the prepared photocatalysts, the one using P6 as a support performed the best, displaying excellent photocatalytic and recycling performance under the irradiation of blue light at 30 °C.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions

This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.

Benzyloxycalix[8]arene: A new valuable support for NHC palladium complexes in C-C Suzuki-Miyaura couplings

Benzyloxycalix[8]arene supported catalysts bearing N-heterocyclic carbene palladium complexes on each subunit were readily synthesized. Intermediates and catalysts were fully characterized, allowing for a fine control of their structure. X-ray diffraction analysis confirmed the formation of a calix[8]arene bearing eight well-defined NHC palladium complexes. The macrocyclic structure of calix[8]arenes allowed for a scalable and chromatography-free catalyst synthesis under homogeneous conditions, while the catalytic reaction proceeded under heterogeneous conditions, just by changing the nature of the solvent. Indeed, when used as a suspension in ethanol, a high TON and TOF were obtained through a large panel of functionalized brominated substrates in C-C Suzuki-Miyaura couplings, with low metal contamination after simple filtration.

Bis-benzimidazolium-palladium system catalyzed Suzuki-Miyaura coupling reaction of aryl bromides under mild conditions

Bis-benzimidazolium salts were prepared successfully from commercially available and inexpensive o-phenylenediamine through a series of simple reactions. The bis-NHC-Pd complexes prepared in situ can catalyze Suzuki-Miyaura cross-coupling reaction under very mild conditions in aqueous media with excellent yields. The efficiency of this reaction is demonstrated by its compatibility with a range of functional groups. Di-ortho-substituted biaryls could be accomplished in 89–99% yields. Moreover, the rigorous exclusion of air or moisture is not required in these transformations.

Palladium-phosphine compound in catalyzing the application of the Suzuki reaction

The invention discloses an application of a palladium-phosphine compound to catalysis of Suzuki reaction. The palladium-phosphine compound serving as a catalyst is capable of efficiently catalyzing Suzuki reaction in ethyl alcohol. By virtue of the palladium-phosphine compound, the defects of aqueous phase reaction are overcome; the aqueous phase reaction can be carried out in the presence of an extremely low quantity of catalysts; the palladium-phosphine compound is high in applicability to substrate; the Suzuki reaction can be carried out in the pollution-free environment in the presence of a relatively small quantity of catalysts.

The transition metal compound and a transition metal catalyst composition

Provided are transition metal catalytic systems for preparing ethylene homopolymers or copolymers of ethylene with α-olefins. More specifically, provided are Group 4 transition metal catalysts, which is characterized in that the Group 4 transition metal catalyst comprises around the Group 4 transition metal a cyclopentadiene derivative, and at least one naphthoxide ligand(s) having aryl substituent(s) that function(s) as an electron donor and serve(s) to stabilize the catalyst system by surrounding an oxygen atom that links the ligand to the transition metal at 2-position, and there is no cross-linkage between the ligands; catalytic systems comprising such transition metal catalyst and aluminoxane cocatalyst or boron compound cocatalyst; and processes for preparing ethylene homopolymers or copolymers of ethylene with α-olefins by using the same.

Photocyclization and Photoaddition Reactions of Arylphenols via Intermediate Quinone Methides

A series of five benzannelated derivatives of 2-phenylphenol were prepared, and their photochemistry was investigated. Two of these (3-phenyl-2-naphthol, 10, and 1-phenyl-2-naphthol, 11) were photoinert. For 2-(1-naphthyl)phenol (12) and 1-(1-naphthyl)-2-naphthol (13), ESPT took place to either the 2′-position or the 7′-position of the naphthalene ring to give quinone methides (QMs) that underwent either reverse proton transfer (RPT) or electrocyclic ring closure to give dihydrobenzoxanthenes. The intermediate QMs for 12 and 13 were detected and characterized by laser flash photolysis. For 2-(9-phenanthryl)phenol (14), ESPT took place either to the 5′-position to give a QM that underwent quantitative electrocyclic ring closure to give the corresponding benzoxanthene or to the 10′-position to give a QM that underwent RPT. If the solution contained methanol, the QM produced on ESPT to the 10′-position in 14 could be trapped as the photoaddition product. The compounds studied in this work demonstrate three possible reactions of QMs produced following ESPT to aromatic carbon atoms: (1) reverse proton transfer (RPT) to regenerate starting material; (2) addition of hydroxylic solvents to give the photoaddition product; and (3) electrocyclic ring closure to give benzoxanthene derivatives.