82777-03-5

Basic information

• Product Name: Naphthalene, 1-[1,1'-biphenyl]-4-yl-
• CAS NO: 82777-03-5
• Molecular Formula: C22H16
• Molecular Weight: 280.369
• Mol File: 82777-03-5.mol

Chemical Properties

• CAS DataBase Reference: Naphthalene, 1-[1,1'-biphenyl]-4-yl-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 1-[1,1'-biphenyl]-4-yl-(82777-03-5)
• EPA Substance Registry System: Naphthalene, 1-[1,1'-biphenyl]-4-yl-(82777-03-5)

Safety Data

• Hazardous Substances Data: 82777-03-5(Hazardous Substances Data)

Upstream product

• 1730-04-7 1,8-diiodonaphthalene 
• 1591-31-7 4-iodo-biphenyl 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 630-95-5 1-naphthyldiphenylmethanol 
• 90-11-9 1-Bromonaphthalene 
• 1625-95-2 [1,1'-biphenyl]-4-yl-trimethylstannane 
• 13922-41-3 1-Naphthylboronic acid 
• 92964-54-0 1-(4-hydroxyphenyl)naphthalene 
• 5122-94-1 4-biphenylboronic acid 
• 1449482-60-3 2-[3-(toluene-4-sulfonyl)biphenyl-4-yl]thiophene 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 204530-94-9 1-(4-bromo-phenyl)-naphthalene 
• 98-80-6 phenylboronic acid 
• 1351445-39-0 N,N,N-trimethyl-1-naphthalenaminium trifluoromethanesulfonate 

Relevant articles and documents

Sterically enhanced 2-iminopyridylpalladium chlorides as recyclable ppm-palladium catalyst for Suzuki–Miyaura coupling in aqueous solution

Sterically hindered 2-iminopyridine derivatives and their palladium chlorides complexes are designed and prepared, which efficiently promote the Suzuki–Miyaura coupling (SMC) reaction in aqueous solution. Besides the good to excellent yields and broad substrate scope, these catalysts can be reused for at least four new batches of the substrates. Spontaneous separation of coupling products in the aqueous reaction medium is the additional striking feature of this catalytic process. Furthermore, catalytic performance of palladium complexes bearing the azo-bridged phenyl groups was greatly influenced by the UV irradiation due to the cis/trans photoisomerization of azo unit of the catalysts. In conclusion, titled palladium complexes provide a green, sustainable, cost-effective, and convenient process to synthesize SMC products at multi-gram-scale reaction.

SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION

Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group;preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; andperforming a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.

C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex

We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.

Solid-state Suzuki-Miyaura cross-coupling reactions: Olefin-accelerated C-C coupling using mechanochemistry

The Suzuki-Miyaura cross-coupling reaction is one of the most reliable methods for the construction of carbon-carbon bonds in solution. However, examples for the corresponding solid-state cross-coupling reactions remain scarce. Herein, we report the first broadly applicable mechanochemical protocol for a solid-state palladium-catalyzed organoboron cross-coupling reaction using an olefin additive. Compared to previous studies, the newly developed protocol shows a substantially broadened substrate scope. Our mechanistic data suggest that olefin additives might act as dispersants for the palladium-based catalyst to suppress higher aggregation of the nanoparticles, and also as stabilizer for the active monomeric Pd(0) species, thus facilitating these challenging solid-state C-C bond forming cross-coupling reactions.

Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous phase Suzuki-Miyaura couplings

In this work, three ligands produced from amino acids were synthesized and used to produce five bis- and PEPPSI-type palladium-NHC complexes using a novel synthesis route from sustainable starting materials. Three of these complexes were used as precatalysts in the aqueous-phase Suzuki-Miyaura coupling of various substrates displaying high activity. TEM and mercury poisoning experiments provide evidence for Pd-nanoparticle formation stabilized in water.

Iodine-Promoted Metal-Free Aromatization: Synthesis of Biaryls, Oligo p-Phenylenes and A-Ring Modified Steroids

We describe efficient procedures based on the use of iodine for the synthesis of biaryls from arylcyclohexenols or arylcyclohexanols using sub-stoichiometric/catalytic iodine and dimethyl sulfoxide (DMSO) as oxidant. Heteroarylcyclohexanols also produced the corresponding biaryl products. It was proven that biphenyl can also be efficiently obtained when the quantity of iodine was reduced to 0.05 equiv. The method is compatible with different functional groups in the aromatic ring (either electron-donating or electron-withdrawing groups). For substrate scope, apart from cyclohexanone and cyclohexenone, some substituted cyclohexanones were also used to synthesize the starting arylcyclohexanols. The process was applied to the synthesis of oligo p-phenylenes and A-ring aromatized steroids, where the combined use of I2/DMSO not only provoked the necessary migration of the methyl group at C-10, but also further extended the conjugation.

One-pot synthesis of functionalized p-terphenyl derivatives

A one-pot synthetic route for preparing functionalized p-terphenyl derivatives 1 and 4 is developed. The route is easily carried from the treatment of cinnamyl aldehydes 2 with substituted allylsulfones 3 in good yields via the tandem intermolecular aldol condensation/intramolecular electrocyclization/ oxidative dehydrogenation.

Exploring the selectivity of the Suzuki-Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes

A series of 1-arylnaphthalenes and 1,8-diarylnaphthalenes were synthesized by the Suzuki-Miyaura cross-coupling methodology showing significant differentiation in the yields and selectivity between aryl rings with electron donating (higher yields), and el

Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions

A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N′-bis(2,6- diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N′-bis(2,6- diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me2, Ph] have been synthesized and fully characterized. When compared to (NHC)Pd(allyl)Cl, substitution at the terminal position of the allyl scaffold favors a more facile activation step. This translates into higher catalytic activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions, allowing for the coupling of unactivated aryl chlorides at room temperature in minutes. In the Suzuki-Miyaura reaction, aryl triflates, bromides, and chlorides react with boronic acids using very low catalyst loading. In the N-aryl amination reaction, a wide range of substrates has been coupled efficiently; primary-, secondary-, alkyl-, or aryl-amines react in high yields with unactivated, neutral, and activated aryl chlorides and bromides. In both reactions, extremely hindered substrates such as tri-ortho-substituted biaryls and tetra-ortho-substituted diarylamines can be produced without loss of activity. Finally, the present catalytic system has proven to be efficient with as low as 10 parts-per-million (ppm) of precatalyst in the Buchwald-Hartwig reaction and 50 ppm in the Suzuki-Miyaura reaction.

Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols

A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.