Synthesis Of Diaryl Ethers Research Articles

Palladium N-Heterocyclic Carbene Catalysts for Synthesis of Diaryl Ethers

Novel functionalized 1,3-dialkylimidazolinium (LH) salts as precursors for N-heterocyclic carbenes (NHCs) have been prepared and successfully applied in the palladium-catalyzed synthesis of diaryl ethers and arylation of benzaldehydes. An efficient catalyst system was prepared in situ from Pd(OAc)2, 1,3-dialkylimidazolinium bromides (LHBr), and NaH.

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

Verdrillte Ether: Die Einführung eines sperrigen Alkylsulfinylsubstituenten ortho zur C-O-Achse eines Diarylethers erzeugt eine starke Konformationspräferenz (siehe Schema). Diese bleibt bei der Oxidation des Sulfoxids zum Sulfon erhalten, sodass eine thermodynamische Racematspaltung der Ether möglich wird. Damit gelang die erste enantioselektive Synthese eines atropisomeren Diarylethers, der nicht Teil eines Makrocyclus ist. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2008/z705660_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C–O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring.

P( i-BuNCH 2CH 2) 3N: an efficient promoter for the microwave synthesis of diaryl ethers

With the title proazaphosphatrane as a promoter, the coupling of aryl fluorides with aryl TBDMS ethers under microwave conditions gave moderate to high yields of the desired products at low catalyst loadings and in short times. In this methodology, electron deficient aryl fluorides possessing substituents, such as nitro, cyano, and ester, were coupled with sterically demanding aryl TBDMS ethers as well as with aryl TBDMS ethers bearing a variety of functionalities such as methoxy, halo, and cyano groups.

The Synthesis of Diaryl Ethers Using Copper Nanoparticles

The Synthesis of Diaryl Ethers Using Copper Nanoparticles

Diaryl ether synthesis in supercritical carbon dioxide in batch and continuous flow modes

A high yielding, batch mode synthesis of diaryl ethers and sulfides by an S(N)Ar fluoride-mediated process in scCO(2) has been developed; the use of a polymer-supported imidazolium fluoride reagent in batch mode led to the development of a fixed-bed continuous flow process, with high conversions.

Highly Efficient Copper-Catalyzed O-Arylation Using Readily Available (S)-N-Methylpyrrolidine-2-Carboxamide as the Ligand

A highly efficient and readily available catalyst system for O-arylation of various phenols using CuI and ( S)- N-methylpyrrolidine-2-carboxamide (Pro-NHMe) was developed. The reaction is widely applicable to the synthesis of diaryl ethers

An efficient BINAM–copper(II) catalyzed Ullmann-type synthesis of diaryl ethers

A wide range of diaryl ethers are synthesized from the corresponding aryl iodides and phenols through Ullmann type coupling reactions in the presence of a catalytic amount of easily available BINAM–Cu(OTf) 2 complex under mild reaction conditions. Less reactive aryl bromides have also been shown to react with phenols under identical reaction conditions to give good yields of the diaryl ethers without increasing the reaction temperature and time.

Ullmann Reaction in Tetraethyl Orthosilicate: A Novel Synthesis of Triarylamines and Diaryl Ethers.

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Cu-nanoparticle catalyzed O-arylation of phenols with aryl halides via Ullmann coupling

Recyclable Cu-nanoparticles provide an efficient, economic, and novel method for the synthesis of diaryl ethers via Ullmann type coupling. This method provides a wide range of substrate applicability and avoids the use of a heavy metal co-catalyst and gives diaryl ethers in satisfactory yields.

Synthesis of ethyl 3-(hydroxyphenoxy)benzyl butylphosphonates as potential antigen 85C inhibitors

All three isomers of ethyl 3-(hydroxyphenoxy)benzyl butylphosphonates as potential antigen 85C inhibitors were synthesized from 3-bromobenzoic acid using Ullman diaryl ether synthesis combined with benzyl- and trityl protection strategy for the phenol hydroxyl groups.

Microwave‐Assisted Construction of Diaryl Ethers Directly from Arylmethanesulfonates as Convenient Latent Phenols with Aryl Halides

The microwave‐assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6–9 min), and good to excellent yields (53–90%) with the wide substrate scope were achieved without any catalyst.

C(aryl)-O Bond Formation from Aryl Methanesulfonates via Consecutive Deprotection and SNAr Reactions with Aryl Halides in an Ionic Liquid

An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methane-sulfonates and a nucleophilic aromatic substitution (S(N)Ar) with activated aryl halides.

A General, Highly Efficient Ullmann C‐O Coupling Reaction under Microwave Irradiation and the Effects of Water

AbstractA general, rapid and highly efficient method for the synthesis of diaryl ethers under the assistance of microwave irradiation was described. A series of diaryl ethers were prepared by direct coupling of phenols and aryl halides in good to excellent yields in anhydrous DMF or NMP at 150 °C within 20 min. The presence of water was found to have a significant impact on the Ullmann C‐O coupling reaction between aryl halides and phenols under microwave irradiation.

Synthesis of diaryl ethers based on one-pot [3+3] cyclizations of 1,3-bis(silyl enol ethers)

Functionalized and sterically encumbered diaryl ethers were prepared by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-aryloxy-3-(silyloxy)alk-2-en-1-ones.

New Copper‐Mediated O‐Arylations of Phenols with Arylstannanes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

A mild and efficient ultrasound-assisted synthesis of diaryl ethers without any catalyst

Diaryl ethers have been prepared by a mild and efficient S NAr reaction by coupling of various phenols including that having a electron-withdrawing group with activated fluoroarenes using sonication in good to excellent yields at very low temperature (58 °C) under catalyst-free.

Ullmann reaction in tetraethyl orthosilicate: a novel synthesis of triarylamines and diaryl ethers

A novel synthesis of triarylamines and diaryl ethers is reported; a feature of this process is the ligand-free copper-catalysed C-N and C-O bond formation in tetraethyl orthosilicate.

Synthesis of novel diaryl ethers and their evaluation as antimitotic agents

A series of novel diaryl ethers possessing various functional groups were synthesized and evaluated for antiproliferative activity in human myeloid leukemia HL-60 cells. Among the compounds examined, compounds 10, 17, 20, 24, and 33 showed moderate to potent antiproliferative activity. These derivatives were further examined in terms of their abilities to inhibit tubulin polymerization; however, all of the tested compounds were relatively ineffective. The reference compound E7010 with an IC 50 of 0.34 μM exhibited potent antiproliferative activity and significantly inhibited tubulin polymerization in a dose-dependent manner.

New copper-mediated O-arylations of phenols with arylstannanes

A novel method for the synthesis of diaryl ethers with phenols and arylstannanes under mild conditions is described. This copper-mediated O-arylation is feasible using DMAP in acetonitrile and is complementary to the use of boronic acids as aryl donors. The reaction is tolerant of a wide range of substituents and sterically hindered coupling partners.