67698-81-1Relevant academic research and scientific papers
Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation
Tran, Ba L.,Fulton, John L.,Linehan, John C.,Lercher, Johannes A.,Bullock, R. Morris
, p. 8441 - 8449 (2018/08/17)
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.
Conversion of Cyclohexanones to Alkyl Aryl Ethers by Using a Pd/C–Ethylene System
El-Deeb, Ibrahim Yussif,Tian, Miaomiao,Funakoshi, Tatsuya,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 409 - 413 (2017/01/24)
The conversion of cyclohexanone and substituted cyclohexanones into alkyl aryl ethers by using a Pd/C–ethylene system is discussed, with ethylene functioning as a hydrogen acceptor. The ether products are easily transformed into the corresponding phenols by treatment with BBr3. The direct conversion of cyclohexenone into phenol in the presence of a catalytic amount of Pd/C under an ethylene atmosphere is also described.
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.
Base catalyzed Mitsunobu reactions as a tool for the synthesis of aryl sec-alkyl ethers
Manivel, Pitchai,Rai, Neithnadka Premsai,Jayashankara, Vaderapura Puttaramegowda,Arunachalam, Pirama Nayagam
, p. 2701 - 2705 (2008/02/03)
A facile and versatile method for the synthesis of aryl sec-alkyl ethers from phenols with alcohols in the presence of base via a Mitsunobu reaction is described.
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.
Use of sonication for the coupling of sterically hindered substrates in the phenolic Mitsunobu reaction
Lepore, Salvatore D.,He, Yuanjun
, p. 8261 - 8263 (2007/10/03)
A vast rate increase in the Mitsunobu reaction of phenols with alcohols where either or both are sterically hindered has been achieved by the use of high concentration combined with sonication.
ORTHO-ALKYLATION OF o-, m-, AND p-CRESOLS WITH CYCLOHEXENE IN THE PRESENCE OF ALUMINUM CRESOLATES
Kozlikovskii, Ya. B.,Koshchii, V. A.,Butov, S. A.,Sokolova, A. V.
, p. 1702 - 1707 (2007/10/02)
The reaction of o-, m-, and p-cresols with cyclohexene in the presence of the corresponding aluminum cresolates leads to mixtures of ethers and phenols, in which the ortho-alkylation products, formed with yields of 75-85percent, predominate.
