Copper-catalyzed Ullmann coupling under ligand- and additive- free conditions. Part 1: O-Arylation of phenols with aryl halides

Chang, Joyce Wei Wei; Chee, Sheena; Mak, Shiya; Buranaprasertsuk, Pongchart; Chavasiri, Warinthorn; Chan, Philip Wai Hong

doi:10.1016/j.tetlet.2008.01.062

Cited by 67 publications

(27 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Under the same conditions, nitrobenzene also showed a relatively low conversion (around 43%), whereas acetonitrile led to a much higher conversion (75%), although still lower than the 100% conversion attained with DMF in hardly 1.5 h of reaction. These results are in good agreement with the literature using other MOF materials [20], homogeneous catalysts [12] and different Ullman reactions [4,29,30]. The solvent has also an important effect on homogeneous Ullmann O-arylation reactions of phenol with aryl chlorides using copper bromide in the presence of 1,10-phenantroline as ancillary ligand (L) [31].…”

Section: Resultssupporting

confidence: 88%

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

et al. 2017

View full text Add to dashboard Cite

The activity and recyclability of Cu-MOF-74 as a catalyst was studied for the ligand-free C–O cross-coupling reaction of 4-nitrobenzaldehyde (NB) with phenol (Ph) to form 4-formyldiphenyl ether (FDE). Cu-MOF-74 is characterized by having unsaturated copper sites in a highly porous metal-organic framework. The influence of solvent, reaction temperature, NB/Ph ratio, catalyst concentration, and basic agent (type and concentration) were evaluated. High conversions were achieved at 120 °C, 5 mol % of catalyst, NB/Ph ratio of 1:2, DMF as solvent, and 1 equivalent of K2CO3 base. The activity of Cu-MOF-74 material was higher than other ligand-free copper catalytic systems tested in this study. This catalyst was easily separated and reused in five successive runs, achieving a remarkable performance without significant porous framework degradation. The leaching of copper species in the reaction medium was negligible. The O-arylation between NB and Ph took place only in the presence of Cu-MOF-74 material, being negligible without the solid catalyst. The catalytic advantages of using nanostructured Cu-MOF-74 catalyst were also proven.

show abstract

Section: Resultssupporting

confidence: 88%

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Calix [4]resorcinarenes is a compound which could be obtained from the reaction of an aldehyde with resorcinol. Some aldehydes which have been used for the synthesis of calix [4] [35][36] , transition metal-free synthesis of aryl ethers 37 and room-temperature ionic liquid-promoted Williamson synthesis of ethers 38 . Meanwhile, the using of a catalyst copper(II) was also reported in the synthesis of ether from aliphatic alcohols and potassium organotrifuoroborate salts 39 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of 4-Phenacyloxy Benzaldehyde Derivatives

Rastuti¹,

Siswanta²,

Jumina³

2016

Orient. J. Chem

View full text Add to dashboard Cite

Some new 4-phenacyloxy benzaldehyde derivatives (PB1-PB4) have been synthesized through substitution reaction of 4-hydroxy-benzaldehyde derivatives and phenacyl bromide derivatives using triethylamine as the catalyst in the micellar media at room temperature. Physical data from IR, 1 H-NMR, 13 C-NMR and GC-MS were used to characterize the compounds structure. The yield of the PB1-PB4 compounds was 46-66% with purity of 91-96%. The compounds have been tested as an antibacterial agent.

show abstract

“…Due to the high costs associated with palladium based catalyst systems, the past decade has seen the development of a multitude of copper catalysts for Ullmann-type O-arylation reactions [11,12,13,14] and the area has been thoroughly reviewed [15,16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of New Compounds NSAIDs-Like Using a Heterogeneous Recyclable Catalyst

Alkayal

Keshe

Madwar

et al. 2016

ILCPA

View full text Add to dashboard Cite

ABSTRACT. In this research, Phenol derivatives have been reacted with aryl halides using 5 mol% Cu(I) Complex [CuClPPh 3 ] 4 as catalyst supported on Amberlyst A21. The typical reaction has been performed between p-cresol and bromobenzene. This reaction is achieved in o-xylene as solvent. However, the catalyst complex does not dissolve in o-xylene rather it acts as heterogeneous catalyst. Therefore, it is filtrated at the end of the reaction and reused several times. Accordingly, new compounds were prepared by reacting some of bromoaryl derivatives with some Phenol derivatives. It is anticipated that the synthesized compounds have a structure NSAIDs-likes that may find their applications in the pharmaceutical industries.

show abstract

Copper-catalyzed Ullmann coupling under ligand- and additive- free conditions. Part 1: O-Arylation of phenols with aryl halides

Cited by 67 publications

References 45 publications

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

A Recyclable Cu-MOF-74 Catalyst for the Ligand-Free O-Arylation Reaction of 4-Nitrobenzaldehyde and Phenol

Synthesis and Characterization of 4-Phenacyloxy Benzaldehyde Derivatives

Synthesis and Structure of New Compounds NSAIDs-Like Using a Heterogeneous Recyclable Catalyst

Contact Info

Product

Resources

About