2052-13-3Relevant academic research and scientific papers
MCM-41-immobilized 1,10-phenanthroline-copper(i) complex: A highly efficient and recyclable catalyst for the coupling of aryl iodides with aliphatic alcohols
Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
, p. 85186 - 85193 (2016/10/12)
A heterogeneous C-O coupling reaction between aryl iodides and aliphatic alcohols was achieved in neat alcohol or toluene at 110 °C in the presence of 10 mol% of the MCM-41-immobilized 1,10-phenanthroline-copper(i) complex [MCM-41-1,10-phen-CuI] with Cs2CO3 as a base, yielding a variety of aryl alkyl ethers in good to excellent yields. The new heterogeneous copper catalyst can easily be prepared by a simple procedure from commercially available and inexpensive reagents, and recovered by filtration of the reaction solution and recycled at least 8 times without significant loss of activity.
Alkoxylation reactions of aryl halides catalyzed by magnetic copper ferrite
Yang, Shuliang,Xie, Wenbing,Zhou, Hua,Wu, Cunqi,Yang, Yanqin,Niu, Jiajia,Yang, Wei,Xu, Jingwei
supporting information, p. 3415 - 3418 (2013/04/23)
Copper ferrite (CuFe2O4), which is easy-made, air-stable, low cost, easy separable, and regenerable, was applied as catalyst in an efficient method for C-O coupling reactions between various kinds of unactivated alkyl alcohols and aryl halides. This method only adopts 2.5% mol CuFe2O4 catalyst and selectively proceeds to C-O bond formation even sensitive substituents exist in the system.
A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols
Gowrisankar, Saravanan,Sergeev, Alexey G.,Anbarasan, Pazhamalai,Spannenberg, Anke,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 11592 - 11598 (2010/10/02)
An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is the synthesis and exploitation of the novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction of aryl halides including activated, nonactivated, and (hetero)aryl bromides as well as aryl chlorides with primary alcohols gave the corresponding alkyl aryl ethers in high yield. Noteworthy, functionalizations of primary alcohols in the presence of secondary and tertiary alcohols proceed with excellent regioselectivity.
Copper-catalyzed etherification of aryl iodides using KF/Al 2O3: An improved protocol
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
, p. 1101 - 1104 (2007/10/03)
A simple and efficient method for the coupling of aryl iodides with aliphatic alcohols and phenols that does not require the use of alkoxide bases is described. This C-O bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al2O 3 comprises an extremely efficient and general catalyst system for the etherification of aryl iodides. Different functionalized aryl iodides were coupled with alcohols and phenols using this method.
Zinc-catalyzed Williamson ether synthesis in the absence of base
Paul, Satya,Gupta, Monika
, p. 8825 - 8829 (2007/10/03)
A zinc-catalyzed Williamson ether synthesis is described with microwave heating in the presence of DMF or stirring in an oil-bath using THF as solvent and in the absence of base. Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations.
Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
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, (2015/03/06)
The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.
Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.
Wolter, Martina,Nordmann, Gero,Job, Gabriel E,Buchwald, Stephen L
, p. 973 - 976 (2007/10/03)
[reaction: see text] A simple and mild method for the coupling of aryl iodides and aliphatic alcohols that does not require the use of alkoxide bases is described. The reactions can be performed in neat alcohol. For more precious alcohols, the etherificat
A reinvestigation of the reaction of arylcalcium iodides with nitrous oxide
Hanusa, Timothy P.
, p. 2435 - 2436 (2007/10/02)
The previously reported reaction of phenylcalcium iodide with N2O in ether to form products with aryl-N bonds has been reexamined with various solvents and methylated aryliodides. The yield of azobenzene is maximized using DME as the solvent, and the insertion reactions may involve diorganocalcium (Ar2Ca) intermediates.
