- Bronsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins
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(Chemical Equation Presented) Intermolecular addition of phenols, carboxylic acids, and protected amines to inert olefins can be catalyzed by low concentrations (1-5%) of triflic acid. Functional groups, such as the methoxyl substitution on aromatics, could be tolerated if the concentration of triflic acid and the reaction temperature are controlled appropriately. This reaction provides one of the simplest olefin addition methods and is an alternative to metal-catalyzed reactions.
- Li, Zigang,Zhang, Junliang,Brouwer, Chad,Yang, Cai-Guang,Reich, Nicholas W.,He, Chuan
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Read Online
- Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation
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We report the arene hydrogenation of ethers, amides, and esters at room temperature and low hydrogen pressure, starting from [(CAAC)Rh(COD)Cl] (CAAC = cyclic alkyl amino carbene). Kinetic, mechanistic, and Rh K-edge XAFS studies showed formation of Rh nanoparticles from [(CAAC)Rh(COD)Cl], in contrast to a previous report of [(CAAC)Rh(COD)Cl] functioning as a homogeneous catalyst for arene hydrogenation. We determined that the site-selective arene hydrogenation catalyzed by this system is under steric control, as shown by detailed competition experiments with derivatives of ethers, amides, and esters bearing different aromatic rings of varying electronic and steric influence. This work illustrates the potential of CAAC ligands in the formation and stabilization of a colloidal dispersion of stable nanoparticle catalysts.
- Tran, Ba L.,Fulton, John L.,Linehan, John C.,Lercher, Johannes A.,Bullock, R. Morris
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p. 8441 - 8449
(2018/08/17)
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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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- 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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- Copper Catalyzed sp3 C-H Etherification with Acyl Protected Phenols
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A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato copper(II) phenolates [CuII]-OAr play a key role in this C-O bond forming reaction, formed via transesterification of AcOAr with [CuII]-OtBu intermediates generated upon reaction of [CuI] with tBuOOtBu.
- Salvador, Tolani K.,Arnett, Charles H.,Kundu, Subrata,Sapiezynski, Nicholas G.,Bertke, Jeffery A.,Raghibi Boroujeni, Mahdi,Warren, Timothy H.
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supporting information
p. 16580 - 16583
(2017/01/10)
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- Copper and l-sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides
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CuSO4·5H2O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield.
- Song, Guang-Lin,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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supporting information
p. 8823 - 8829
(2015/10/20)
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- Fe3O4@mesoporouspolyaniline: A highly efficient and magnetically separable catalyst for cross-coupling of aryl chlorides and phenols
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A high surface, magnetic Fe3O4@mesoporouspolyaniline core-shell nanocomposite was synthesized from magnetic iron oxide (Fe 3O4) nanoparticles and mesoporouspolyaniline (mPANI). The novel porous magnetic Fe3O4 was obtained by solvothermal method under sealed pressure reactor at high temperature to achieve high surface area. The mesoporouspolyaniline shell was synthesized by in situ surface polymerization onto porous magnetic Fe3O4 in the presence of polyvinylpyrrolidone (PVP) and sodium dodecylbenzenesulfonate (SDBS), as a linker and structure-directing agent, through 'blackberry nanostructures' assembly. The material composition, stoichiometric ratio and reaction conditions play vital roles in the synthesis of these nanostructures as confirmed by variety of characterization techniques. The role of the mesoporouspolyaniline shell is to stabilize the porous magnetic Fe3O4 nanoparticles, and provide direct access to the core Fe3O4 nanoparticles. The catalytic activity of magnetic Fe3O 4@mesoporousPANI nanocomposite was evaluated in the cross-coupling of aryl chlorides and phenols. Copyright
- Arundhathi,Damodara,Likhar, Pravin R.,Kantam, M. Lakshmi,Saravanan,Magdaleno, Travis,Kwon, Sun Hee
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supporting information; experimental part
p. 1591 - 1600
(2011/08/03)
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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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- SUBSTITUTED DIHYDRO AND TETRAHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF
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The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.
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Page/Page column 30
(2010/04/23)
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- Efficient catalytic activity of copper/aluminum hydrotalcite in diaryl ether synthesis
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A simple copper/aluminum hydrotalcite (Cu/Al-HT) catalyzed arylation of phenols with aryl iodides afforded the corresponding diaryl ethers in moderate to excellent yields. This ligand- free Cu/Al-HT catalyzed coupling of aryl iodides with phenols resulted in high yields of diaryl ethers in the absence of an additive. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles. Georg Thieme Verlag Stuttgart New York.
- Sreedhar,Arundhathi,Reddy, M. Amarnath,Kantam, M. Lakshmi
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experimental part
p. 483 - 487
(2009/07/11)
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- An efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols
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A wide range of alkyl aryl ethers are synthesized from the corresponding aryl iodides and aliphatic alcohols through Ullmann-type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-CuI complex. Less reactive aryl bromides have also been shown to react with aliphatic alcohols under identical reaction conditions to give good yields of the alkyl aryl ethers without increasing the reaction temperature and time.
- Naidu, Ajay B.,Sekar
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p. 3147 - 3151
(2008/09/20)
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- Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins
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Ph3PAuOTf can catalyze efficient intermolecular addition of phenols and carboxylic acids to olefins under relatively mild conditions. Copyright
- Yang, Cai-Guang,He, Chuan
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p. 6966 - 6967
(2007/10/03)
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