55382-49-5

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 71-43-2 benzene 
• 553-82-2 1,3-dichloro-4-methoxybenzene 
• 591-50-4 iodobenzene 
• 60633-25-2 2-bromo-4-chloroanisole 
• 98-80-6 phenylboronic acid 
• 90-43-7 2-Phenylphenol 
• 19434-42-5 4-amino-6-phenylphenol 
• 607-12-5 5-chloro-biphenyl-2-ol 
• 77-78-1 dimethyl sulfate 
• 696-62-8 para-iodoanisole 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 607-12-5 5-chloro-biphenyl-2-ol 

Relevant academic research and scientific papers

Search for a photoinduced (site-selective) cleavage of the Ar-Cl bond in dichloroanisoles

The site-selective cleavage of an Ar-X bond in polyhalogenated aromatics is an important tool in synthetic planning especially when more than one identical halogen atom is present. An alternative to the usual metal-catalyzed cleavage is represented by photochemistry although only a few examples have been reported. We then investigated the feasibility of the site-selective photodechlorination of some dichloroanisoles through a combined experimental and computational study. In the case of 2,4-dichloroanisole, selective detachment of the chlorine atom at the ortho position with respect to the OMe group was observed upon photohomolysis (in cyclohexane) or photoheterolysis (in MeOH) of the Ar-Cl bond. In the latter case, 5-chloro-2-methoxy-1,1′-biphenyl was exclusively formed upon reaction of the resulting phenyl cation with benzene. The substitution of an OH group for a OMe group was detrimental since a lower photoreactivity resulted with no improvement in the selectivity.

Direct ortho Arylation of Anisoles via the Formation of Four-Membered Lithiumcycles/Palladacycles

We report here our latest discovery on the directed lithiation and palladium-catalyzed arylation of anisoles. During this research, the formation of a four-membered lithiumcycle followed by transmetalation to the corresponding palladacycle has been achieved, which is difficult to be obtained from palladium-catalyzed C-H activation processes. This approach has provided an alternative way of introducing functionalities to arenes such as anisoles, thioanisoles, and anilines. This approach also features an excellent monoselectivity compared with reactions under transition-metal-catalyzed conditions.

Condensed-cyclic compound and organic light emitting diode comprising the same

Disclosed are a condensed-ring compound and an organic light-emitting device comprising the same. The condensed-ring compound is represented by chemical formula 1. The organic light-emitting device comprising the condensed-ring compound can have low driving voltage, high efficiency, high brightness, and long durability.COPYRIGHT KIPO 2016

Synthesis, structure, and catalytic applications for ortho - And meta -carboranyl based NBN pincer-Pd complexes

o- and m-Carborane-based NBN pincer palladium complexes (oCB-L1)Pd, (oCB-L2)Pd, and (mCB-L1)Pd are synthesized in two steps from commercially available starting materials. The pincer complexes were prepared by the reaction of bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl oCB-L1, 6-methyl-2-pyridyl oCB-L2) or bis-[2-pyridyl (hydroxy)methyl]-1,2-dicarba-meta- dodecaborane (mCB-L1) with [PdCl2(MeCN)2] under mild conditions. The X-ray structure determination of all carboranyl pincer complexes shows unambiguously B-H activation of the carborane cages. The results agree with the Pd-B bonds in all complexes exhibiting strong σ-electron donation. Theoretical calculations reveal the importance of considering the solid state intermolecular hydrogen bonding when investigating the trans influence in organometallic chemistry. A localized orbitals approach has also been applied to analyze the metal oxidation state in the carboranyl pincer complexes. Catalytic applications of (oCB-L1)Pd and (mCB-L1)Pd have shown the complexes are good catalyst precursors in Suzuki coupling in water and with very low amounts of catalyst loadings.

The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance

The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.

Dichloro-bis(aminophosphine) complexes of palladium: Highly convenient, reliable and extremely active suzuki-miyaura catalysts with excellent functional group tolerance

Dichloro-bis(aminophosphine) complexes are stable depot forms of palladium nanoparticles and have proved to be excellent SuzukiMiyaura catalysts. Simple modifications of the ligand (and/or the addition of water to the reaction mixture) have allowed their formation to be controlled. Dichlorobis[1- (dicyclohexylphosphany1)piperidine]palladium (3), the most active catalyst of the investigated systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1-1.2 equiv) of arylboronic acid at 80°C in the presence of 0.2 mol % of the catalyst in technical grade toluene in flasks open to the air. Conversions of >95% were generally achieved within only a few minutes. The reaction protocol presented herein is universally applicable. Side-products have only rarely been detected. The catalytic activities of the aminophosphine-based systems were found to be dramatically improved compared with their phosphine analogue as a result of significantly faster palladium nanoparticle formation. The decomposition products of the catalysts are dicyclohexylphosphinate, cyclohexylphosphonate, and phosphate, which can easily be separated from the coupling products, a great advantage when compared with non-water-soluble phosphine-based systems.

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

A general gold-catalyzed oxidative homo- and hetero-coupling of arenes in mild conditions is described. This reaction gives moderate to excellent yield using PhI(OAc)2 as an oxidant. The effects of temperature, solvent, oxidant and concentration of substrate in this process have also been studied in detail. The product identity and distribution as well as the substrate limitation give us insights into this type of gold catalysts. Depending upon the reaction conditions, the gold catalyst behaves as a simple Lewis acid, which produces amines from arenes using DIAD as an aminating reagent.

PHENYLATION CATIONIQUE DU CHLORO-4 ANISOLE, ETUDE DE LA MIGRATION DU CHLORE ET DU PHENYLE DANS LES CATIONS IPSO-ARENIUM.

The phenyl cations obtained from the thermolysis of benzenediazonium tetrafluoroborate react with 4-chlroanisole to give, in addition to phenylation products at position 2 and 3, 2-chloro-4-methoxybiphenyl.The latter is formed by the attack of C6H5(1+) ipso to the chlorine followed by 1,2 migration of the halogen.This rearrangement is totally suppressed in nucleophilic solvents such as dimethylsulfoxide, whereas it is important in heterogeneous conditions.The ability of DMSO to trap the ipso-arenium ions has provided indirect evidence for the attack of C6H5(1+) ipso to the methoxy group. 1-2 migration of the phenyl group has been observed in arenium ions formed by attack of C6H5(1+) ipso to the chlorine and ipso to the methoxy group. 4-methoxybiphenyl and 2,4-dichloroanisole have not been detected by G L C so that dechlorophenylation of 4-chloroanisole must be negligible.