5349-18-8Relevant academic research and scientific papers
Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides
Guo, Ying,Fan, Xue-Min,Nie, Min,Liu, Hong-Wei,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
, p. 4744 - 4755 (2015/08/03)
An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.
Catalytic alkylation of cresols with propanol-1
Tagiev,Agaeva,Nazarova
, p. 1252 - 1255 (2014/02/14)
Study of the reaction of alkylation of ortho-, meta-, and para-cresols with propanol-1 in the presence of ferrite cobalt and manganese catalysts is reported. The effect of the catalyst composition and reaction conditions on the yield and isomeric composit
Reductive cleavage versus hydrogenation of allyl aryl ethers and allylic esters using sodium borohydride/catalytic ruthenium(III) in various aqueous solvent mixtures
Babler, James H.,White, Nicholas A.,Kowalski, Eric,Jast, Jeffrey R.
experimental part, p. 745 - 748 (2011/03/21)
The reduction of allyl aryl ethers using sodium borohydride in the presence of a catalytic amount of ruthenium(III) chloride in various aqueous solvent mixtures at 0 °C was examined. In aqueous tetrahydrofuran, hydrogenation was the favored pathway (85-100% yield of the corresponding aryl propyl ether); whereas in aqueous N-methylformamide, reductive cleavage predominated (4:1 mixture of phenolic product/aryl propyl ether). In order to gain some insight into the mechanism for this process, 3-octyn-1-ol and trans-2-decen-1-yl acetate were subjected to similar reductive conditions; and both substrates afforded products inconsistent with a single-electron-transfer mechanism.
Heterogeneous phase alkylation of phenols making use of phase transfer catalysis and microwave irradiation
Keglevich, Gyoergy,Balint, Erika,Karsai, Eva,Varga, Judit,Gruen, Alajos,Balint, Maria,Greiner, Istvan
experimental part, p. 535 - 539 (2010/04/23)
The benzylation of cresol was studied under liquid-liquid and solid-liquid phase transfer catalytic conditions. Microwave irradiation was useful only in the solid-liquid phase benzylations. Using acetonitrile as the solvent, the benzylations were fully O-selective, but complete conversions were obtained only in the presence of Cs2CO3. There was no need to use an onium salt. In the absence of solvent, an O-selectivity of ca. 90% could be obtained in the presence of an alkali carbonate and an onium salt. The optimum set of conditions was extended to the reaction of other phenol derivatives and alkylating agents.
Organosoluble copper clusters as precatalysts for carbon - Heteroelement bond-forming reactions: Microwave and conventional heating
Manbeck, Gerald F.,Lipman, Adam J.,Stockland Jr., Robert A.,Freidl, Adrienne L.,Hasler, Amy F.,Stone, Joshua J.,Guzei, Ilia A.
, p. 244 - 250 (2007/10/03)
(Chemical Equation Presented). The coupling of aryl iodides with alcohols under mild conditions has been explored using self-assembled octanuclear copper clusters as catalysts. Reactions involving tetrahydrofurfuryl alcohol were typically complete in 4-8
Alkoxylated p-phenylenevinylene oligomers: Synthesis and spectroscopic and electrochemical properties
Ndayikengurukiye, Henri,Jacobs, Sven,Tachelet, Wim,Van Der Looy, Johan,Pollaris, Anne,Geise, Herman J.,Claeys, Magda,Kauffmann, Jean M.,Janietz, Silvia
, p. 13811 - 13828 (2007/10/03)
Twenty-one n-alkoxy substituted phenylenevinylene oligomers were synthesized, varying in size, number and position of the OR groups. IR,MS and solubility data are presented. NMR measurements provided the molecular structure as well as information about conformations and molecular dynamics. UV and of cyclic voltammetric data give correlations of chemical structure (number and position of OR substituents) with separate HOMO and LUMO energies.
