- MCM-41-immobilized 1,10-phenanthroline-copper(i) complex: A highly efficient and recyclable catalyst for the coupling of aryl iodides with aliphatic alcohols
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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.
- Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
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p. 85186 - 85193
(2016/10/12)
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- A Comparative Ancillary Ligand Survey in Palladium-Catalyzed C-O Cross-Coupling of Primary and Secondary Aliphatic Alcohols
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The utility of RockPhos, Ad-BippyPhos, JosiPhos (CyPF-tBu), and Mor-DalPhos in palladium-catalyzed C-O cross-coupling reactions involving aliphatic alcohols and (hetero)aryl halides under analogous conditions was examined, both at room temperature and at
- Sawatzky, Ryan S.,Hargreaves, Breanna K. V.,Stradiotto, Mark
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p. 2444 - 2449
(2016/06/01)
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- Alkoxylation reactions of aryl halides catalyzed by magnetic copper ferrite
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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.
- Yang, Shuliang,Xie, Wenbing,Zhou, Hua,Wu, Cunqi,Yang, Yanqin,Niu, Jiajia,Yang, Wei,Xu, Jingwei
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supporting information
p. 3415 - 3418
(2013/04/23)
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- A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols
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Forging a bond: An efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands. Copyright
- Wu, Xiaoxing,Fors, Brett P.,Buchwald, Stephen L.
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supporting information; experimental part
p. 9943 - 9947
(2011/12/05)
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- A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols
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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.
- Gowrisankar, Saravanan,Sergeev, Alexey G.,Anbarasan, Pazhamalai,Spannenberg, Anke,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 11592 - 11598
(2010/10/02)
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- Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.
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[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
- Wolter, Martina,Nordmann, Gero,Job, Gabriel E,Buchwald, Stephen L
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p. 973 - 976
(2007/10/03)
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- The use of anion exchange resins for the synthesis of combinatorial libraries containing aryl and heteroaryl ethers
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Quaternary ammonium exchange resins (Amberlite IRA-900) were prepared that contained each a mixture of ten aryloxides and heteroaryloxides. The feasibility of generating combinatorial libraries containing aryl and heteroaryl ethers was demonstrated by reacting the resin's with a single electrophile (n-butyl bromide) to afford mixtures of ether products. The advantages of using quaternary ammonium exchange resins over solution phase chemistry to prepare this library are discussed.
- Parlow, John J.
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p. 5257 - 5260
(2007/10/03)
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