1204-60-0

Usage

Chemical Properties

Light brown to yellow liquid

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 3878, 1986 DOI: 10.1021/jo00370a024

InChI:InChI=1/C13H10O/c14-10-11-5-4-8-13(9-11)12-6-2-1-3-7-12/h1-10H

Upstream product

• 14704-31-5 3-(bromomethyl)-1,1'-biphenyl 
• 69605-90-9 3-phenyl-benzyl alcohol 
• 119924-77-5 Biphenyl-3-carboselenoic acid Se-phenyl ester 
• 103668-97-9 3-phenyl-5,6-dihydrobenzaldehyde 
• 31254-19-0 1-Ethyl-1-phenylallyl alcohol 
• 68-12-2 N,N-dimethyl-formamide 
• 587-04-2 m-Chlorobenzaldehyde 
• 98-80-6 phenylboronic acid 
• 3132-99-8 m-bromobenzoic aldehyde 
• 87199-16-4 3-Formylphenylboronic acid 
• 71-43-2 benzene 
• 2996-92-1 phenyl trimethylsiloxane 
• 93-55-0 1-phenyl-propan-1-one 
• 591-50-4 iodobenzene 

Downstream Products

• 115535-04-1 1,2-di([1,1'-biphenyl]-3-yl)ethane-1,2-dione 
• 873384-69-1 (+/-)-Hydroxy-phenyl-(biphenylyl-⁽³⁾)-methan 
• 60521-26-8 (E)-3-Biphenyl-3-yl-acrylic acid 
• 177976-49-7 3-phenylbenzylamine 
• 60521-26-8 3-(biphenyl-3-yl)acrylic acid 
• 58650-11-6 3-Biphenylylacetylene 
• 875576-61-7 [C₆H₅C₆H₄CH(CH₂CH₃)S]2 
• 698378-24-4 (2R)-2-{[(1R)-1-(1,1'-biphenyl)-3-yl-3-butenyl]amino}-2-phenylethanamide 
• 121801-86-3 3-(Biphenyl-3-yl-chloro-methyl)-benzo[b]thiophene 
• 121802-00-4 1-(Benzo[b]thiophen-3-yl-biphenyl-3-yl-methyl)-1H-imidazole 
• 103266-80-4 2,3-bis-biphenyl-3-yl-quinoxaline 

Relevant academic research and scientific papers

A recyclable heterogeneous nanocatalyst of copper-grafted natural asphalt sulfonate (NAS@Cu): Characterization, synthesis and application in the Suzuki-Miyaura coupling reaction

A new and efficient nanocatalyst was identified, synthesized and introduced and its catalytic activity was investigated in the Suzuki coupling reaction. This nanocatalyst can be synthesized by sulfonating natural asphalt as a high-carbon, cost-effective and accessible substrate using high-concentration sulfuric acid. After being neutralized by NaOH, it was transformed into sodium natural asphalt sulfonate (Na-NAS). Ultimately, the nanocatalyst was synthesized through a displacement reaction of sodium natural asphalt sulfonate with copper chloride. The solid derived (NAS@Cu) was identified using Transmission Electron Microscopy (TEM), Energy Dispersive Spectroscopy (EDS), Scanning Electron Microscopy (SEM), N2 sorption isotherms, Inductively Coupled Plasma (ICP), X-ray Diffraction (XRD), Thermogravimetric Analysis (TGA), Atomic Absorption Spectrometry (AAS) and Fourier-transform Infrared spectroscopy (FT-IR). NAS@Cu is a heterogeneous catalyst with advantages such as having a high specific surface area, being environmentally friendly and economically sound and simple purification and separation from the reaction mixture. Moreover, the nano-catalyst was recycled several times without any significant changes in its catalytic properties. This journal is

Extended architectures constructed of thiourea-modified SBA-15 nanoreactor: A versatile new support for the fabrication of palladium pre-catalyst

We designed and synthesized a novel catalyst consisting of ordered mesoporous silica (SBA-15) functionalized with bis(thiourea) (BTU) linker. The regular and unique pore channels of BTU-SBA-15 ensure proper control of the size and homogeneous distribution of palladium nanoparticles. The physiochemical properties of the hybrid Pd?BTU-SBA-15 pre-catalyst were investigated using various techniques. The proposed catalyst is found to be very active, reusable, stable and scalable, and has excellent reactivity and selectivity for Suzuki and Heck coupling reactions under very mild and sustainable reaction conditions.

The Suzuki reaction under solvent-free conditions

The coupling reaction of diverse arylhalogenids with phenylboronic acid under solvent-free conditions has been performed using a palladium catalyst. The order of reactivity was complementary to the normal Suzuki reaction.

Cross-Linked Thiazolidine Network as Support for Palladium: A New Catalyst for Suzuki and Heck Reactions

A thiazolidine-based material was used for the first time as support for palladium. The support was prepared by starting from a highly cross-linked thiazolium-based material, obtained by radical oligomerization of a bisvinylthiazolium dibromide salt in the presence of 3-mercaptopropyl-modified silica SBA-15. Palladium was immobilized by treatment with tetrachloropalladate salt. Reduction with sodium borohydride afforded a thiazolidine-based material that acted as ligands for the Pd species. The thiazolidine-based palladium catalyst was fully characterized and, working in only 0.1 mol% amount, displayed good activity in the Suzuki-Miyaura and in the Heck reactions. Several biphenyl and alkene compounds could be prepared in high yields. The catalytic material proved to be fully recoverable and it was representatively used for three times in the Suzuki-Miyaura reaction without showing any decrease in its activity.

Immobilized palladium on modified magnetic nanoparticles and study of its catalytic activity in suzuki-miyaura C-C coupling reaction

A new magnetically reusable nanosolid, Fe3O4@PPCA@Pd(0) (PPCA = piperidine-4-carboxylic acid), as a versatile and highly effective catalyst was fabricated and characterized using transmission and scanning electron microscopies, X-ray diffraction, thermogravimetric analysis, Fourier transform infrared and energy-dispersive spectroscopies and vibrating sample magnetometry. This nanosolid shows great catalytic activity for the synthesis of biphenyl compounds in short reaction times and with high yields. The magnetic character of this catalyst allows retrieval and multiple uses without appreciable loss of its catalytic activity. Our system not only solves the basic problems of catalyst separation and recovery, but also the reactions can be performed in green media.

Pd(OAc)2 in WERSA: A novel green catalytic system for Suzuki-Miyaura cross-coupling reactions at room temperature

A recyclable/reusable Pd(OAc)2 catalysed Suzuki-Miyaura cross-coupling reaction condition in neat "Water Extract of Rice Straw Ash" (WERSA) at room temperature was developed. This is a ligand/base/promoter/additive/organic media free protocol.

Nitrogen-doped graphdiyne for effective metal deposition and heterogeneous Suzuki-Miyaura coupling catalysis

For heterogeneous catalysts with nitrogen doped carbon materials as supporting substrates, accurate nitrogen (N) species and content is an important factor for promoting the catalytic activity. In this paper, N-doped graphdiyne (NGDY) was prepared from tetraethynylpyrazine (TEP) by bottom-up synthesis method as the support of metal nanoparticles. Specific pyridine nitrogen atoms are introduced in the N-doped carbon material. This unique structure makes it a promising material to support ultrafine metal particles or clusters. Microwave-assisted anchoring of Pd, Pt, Cu, Ni nanoparticles on NGDY generated novel hybrid composites, in which Pd-NGDY has high versatility for Suzuki-Miyaura reaction. DFT calculations revealed a charge transfer from NGDY to Pd NPs, and the free energy distribution showed a downward trend for Suzuki-Miyaura coupling reactions.

Metformin as a versatile ligand for recyclable palladium-catalyzed cross-coupling reactions in neat water

We present the high catalytic activity of an in situ generated palladium(ii)/metformin complex in neat water for the Suzuki-Miyaura and Sonogashira cross-coupling reactions. These reactions were performed in pure water without any co-solvent or mass transfer agent. The palladium(ii)/metformin complex gave excellent to good yields for the Suzuki-Miyaura coupling reaction and catalyzed with a certain specificity to the aryl iodide coupling in the Sonogashira reaction. The methodology showcases a recyclability up to four catalytic runs for the Suzuki-Miyaura cross-coupling reaction, performed with only 0.5 mol% palladium loading.

Pd(OAc)2@SBA-15/PrEn nanoreactor: A highly active, reusable and selective phosphine-free catalyst for Suzuki-Miyaura cross-coupling reaction in aqueous media

A series of ordered mesoporous organic-inorganic hybrid material was designed by using the amine-functionalized SBA-15 (PdX2@SBA-15/N Y, Y = 1, 2) as solid support for palladium complexes. Among them, the Pd(OAc)2/ethylenediamine complex encapsulated into SBA-15 (Pd(OAc)2@SBA-15/PrEn or Pd(OAc)2@SBA-15/PrNHEtNH 2) exhibits higher activity and selectivity toward Suzuki cross-coupling reaction under aerobic conditions and water solvent mixture. The SBA-15/PrEn supported palladium pre-catalyst could be separated easily from reaction products and used repetitively several times, showing its superiority over homogeneous catalysts for industrial and chemical applications. Copyright

A new functionalized mesoporous matrix supported Pd(ii)-Schiff base complex: An efficient catalyst for the Suzuki-Miyaura coupling reaction

A new Pd(ii) bounded 2D-hexagonally ordered functionalized MCM-41 type material (IV) has been synthesized. Functionalization was carried out by the anchoring of 3-aminopropyltriethoxysilane in the MCM-41 type mesoporous material, followed by grafting with 2,6-diacetylpyridine (DAP) to give a N 3-type Schiff base chelating attachment for the Pd(ii) species. Fourier transform infrared (FTIR), powder X-ray diffraction (PXRD) and high resolution transmission electron microscopy (HRTEM) studies have been used to characterize the material. Material IV behaves as a highly active catalyst towards Suzuki-Miyaura cross-coupling reaction for the synthesis of biaryl organics. In addition, IV acts as a true heterogeneous catalyst in coupling reaction. It was found that this catalyst is highly efficient and recyclable towards Suzuki-Miyaura reaction with high turn over frequencies. X-Ray photoelectron spectroscopic (XPS) analysis was employed to understand the oxidation state of the palladium atom in the catalyst (IV) and its loading in the material. The Royal Society of Chemistry.