Ether synthesis from activated aromatic halides and alkali-metal carbonates

Fukawa, Isaburo; Tanabe, Tsuneaki; Dozono, Tetsuro

doi:10.1039/p29920000377

Cited by 8 publications

(4 citation statements)

References 2 publications

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“…However, access to biphenyl ethers from only one substrate is rare in literature. Most of the methods to date advocate the use of a metal catalyst along with a cocatalyst during biphenyl ether synthesis. , The use of a metal catalyst has its limitation of toxicity for the preparation of biologically active compounds. Herein, we report the synthesis of a series of symmetrical biaryl ethers from activated halo benzenes in an economically and precise way, a few of the unsymmetrical biaryl ethers were also synthesized where activated halo benzenes were used to get the desired product under metal-free conditions.…”

Section: Introductionmentioning

confidence: 99%

Metal- and Phenol-Free Synthesis of Biaryl Ethers: Access to Dibenzobistriazolo-1,4,7-oxadiazonines and Vancomycin-Like Glyco-Macrocycles as Antibacterial Agents

et al. 2018

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Section: Introductionmentioning

confidence: 99%

Metal- and Phenol-Free Synthesis of Biaryl Ethers: Access to Dibenzobistriazolo-1,4,7-oxadiazonines and Vancomycin-Like Glyco-Macrocycles as Antibacterial Agents

et al. 2018

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“…As has been reported in the synthesis of poly(ether ketone) dendrons 31 prepared by using only 1 as the building block, the lower molecular weight impurities in the crude products were regarded to be a compound which was caused by the one-to-one reaction between G − OH and the building block, whereas the higher molecular weight impurities were formed by the reaction of G − OH with an excess amount of the building block and potassium carbonate. The latter reaction has been reported in the synthesis of linear poly(ether ketones). , The relative ratio of these impurities was less than those of poly(ether ketone) dendrons 31 prepared by using only 1 as the building block. The higher selectivity of the coupling reaction of the higher generation, G − OH , may be also ascribed to the lower steric hindrance of the hydroxy group.…”

Section: Resultsmentioning

confidence: 80%

“…The latter reaction has been reported in the synthesis of linear poly(ether ketones). 61,62 The relative ratio of these impurities was less than those of poly-(ether ketone) dendrons 31 prepared by using only 1 as the building block. The higher selectivity of the coupling reaction of the higher generation, G-OH, may be also ascribed to the lower steric hindrance of the hydroxy group.…”

Section: Resultsmentioning

confidence: 92%

Preparation of Poly(ether ketone) Dendrons with Graded Structures

Morikawa

Ono

1999

Macromolecules

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New highly branched poly(ether ketone) dendrons, with graded structures, were synthesized by the convergent approach using aromatic nucleophilic substitution reactions. Four kinds of compounds s 3,5-bis(4-fluorobenzoyl)anisole, 1; 4-methoxy-3′,5′-bis(4-fluorobenzoyl)-biphenyl, 2; 4-methoxy-3′′,5′′-bis-(4-fluorobenzoyl)-p-terphenyl, 3; and 4-methoxy-3′′′,5′′′-bis(4-fluorobenzoyl)-p-quaterphenyl, 4s(numberedin the order of the phenylene length) were used as the building blocks, where the methoxy groups were the protected form of hydroxy groups. The reactions of 1 with phenol gave the first generation dendron, G1. Next, after the methoxy group of G1 was converted to the hydroxy derivative, G1-OH by the reaction with aluminum chloride, the resultant phenol functionality of G1-OH was allowed to react with 2 to yield the second generation dendron: G2. By repeating the procedure, further generations G3 and G4, were prepared using 3 and 4 as the building block, respectively. The 1 H and 13 C NMR spectra were consistent with the structure of these dendrons. The molecular weight and molecular weight distribution determined by gel permeation chromatography indicated that the dendron posessed remarkably narrow molecular weight distribution after purification by silica gel chromatography. The analysis of these structurally unambiguous dendrons by matrix-assisted laser desorption ionization time of flight is described. The structure of the dendrons were demonstrated with a gradient of phenylene chain lengths from the periphery to the core.

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“…The classical method for the synthesis of diaryl ether derivatives is a C-O coupling reaction of phenolic derivatives with a C-X bond. [3][4][5][6] In most cases, transition metals have played a key role in this transformation. Many transition metals, such as Fe, Ir, Rh, Pd and Cu, have shown excellent catalytic activity in this area.…”

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confidence: 99%