103-54-8Relevant articles and documents
Palladium nanoparticles, stabilized by lignin, as catalyst for cross-coupling reactions in water
Coccia, Francesca,Tonucci, Lucia,D'Alessandro, Nicola,D'Ambrosio, Primiano,Bressan, Mario
, p. 12 - 18 (2013)
Palladium nanoparticles of a definite shape (spherical) and dimension (8-14 and 16-20 nm) were prepared employing two water soluble lignin samples as both reducing and stabilizing agent in definitely green experimental conditions, namely aqueous solution, aerobic conditions, moderate temperature, short times. The above nanoparticles were employed as catalyst for a series of carbon-carbon coupling reactions carried out in water at mild conditions. Heck and Suzuki reactions were performed for several substrates, by changing the nature of halogen, the substituents at the aromatic ring, the bases employed and the temperature. Product yields were satisfactory and selectivities very good. Other two cross-coupling reactions, namely Sonogashira and Stille, were also tested: iodine derivatives showed always the best reactivity, while chlorine derivatives did not react.
Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
, p. 4051 - 4053 (2017)
Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
Benzoquinone Cocatalyst Contributions to DAF/Pd(OAc)2-Catalyzed Aerobic Allylic Acetoxylation in the Absence and Presence of a Co(salophen) Cocatalyst
Kozack, Caitlin V.,Tereniak, Stephen J.,Jaworski, Jonathan N.,Li, Bao,Bruns, David L.,Knapp, Spring M. M.,Landis, Clark R.,Stahl, Shannon S.
, p. 6363 - 6370 (2021)
Palladium(II)-catalyzed allylic acetoxylation has been the focus of extensive development and investigation. Methods that use molecular oxygen (O2) as the terminal oxidant typically benefit from the use of benzoquinone (BQ) and a transition-metal (TM) cocatalyst, such as Co(salophen), to support oxidation of Pd0 during catalytic turnover. We previously showed that Pd(OAc)2 and 4,5-diazafluoren-9-one (DAF) as an ancillary ligand catalyze allylic oxidation with O2 in the absence of cocatalysts. Herein, we show that BQ enhances DAF/Pd(OAc)2 catalytic activity, nearly matching the performance of reactions that include both BQ and Co(salophen). These observations are complemented by mechanistic studies of DAF/Pd(OAc)2 catalyst systems under three different oxidation conditions: (1) O2 alone, (2) O2 with cocatalytic BQ, and (3) O2 with cocatalytic BQ and Co(salophen). The beneficial effect of BQ in the absence of Co(salophen) is traced to the synergistic roles of O2 and BQ, both of which are capable of oxidizing Pd0 to PdII. The reaction of O2 generates H2O2 as a byproduct, which can oxidize hydroquinone to quinone in the presence of PdII. NMR spectroscopic studies, however, show that hydroquinone is the predominant redox state of the quinone cocatalyst in the absence of Co(salophen), while inclusion of Co(salophen) maintains oxidized quinone throughout the reaction, resulting in better reaction performance.
Ag-Cu nanoparticles as efficient catalysts for transesterification of β-keto esters under acid/base-free conditions
Yue, Hongmei,Yu, Hao,Liu, Sheng,Xu, Chunli
, p. 19041 - 19051 (2016)
Transesterification of β-keto esters and alcohols are traditionally catalyzed by acid or basic catalysts. However, these traditional catalysts do not always meet the requirements of modern synthetic chemistry which need to be highly efficient, selective, and environmentally friendly. In this work, Ag-Cu metal sites were first introduced as transesterification catalysts. The effect of the support, Ag:Cu molar ratio, and reaction conditions were investigated. The Ag-Cu metal sites were proved to be active in the β-ketoester transesterification with various alcohols, having yields comparable to the conventional acid- or base-catalysts.
Development of a mild and efficient protocol for the protection and O-alkylation of allyl alcohols
Selvakumar, Kodirajan,Prasath Lingam, Kandapalam Arun,Luxmi Varma, Rama Varma
, p. 36538 - 36543 (2014)
An efficient, pyridine-free protocol has been developed for the protection of the 3°-allyl alcohol of oxindole using a mild base, such as potassium carbonate, under microwave irradiation conditions. The methodology has been tested with a variety of substrates and protecting group reagents, which provides a clean and good yield of the desired products within a short reaction time. the Partner Organisations 2014.
Silica chloride as a mild and efficient reagent for acetylation of alcohols
Shirini, Farhad,Zolfigol, Mohammad Ali,Khaleghi, Mahroo
, p. 1999 - 2002 (2003)
A variety of alcohols underwent acetylation with acetic anhydride in the presence of silica chloride. All reactions were performed at room temperature and under completely heterogeneous conditions in good to high yields.
Novel access to carbonyl and acetylated compounds: The role of the tetra-: N -butylammonium bromide/sodium nitrite catalyst
Sheykhan, Mehdi,Moafi, Hadi Fallah,Abbasnia, Masoumeh
, p. 51347 - 51355 (2016)
A novel aerobic oxidation of alcohols without the use of any oxidants was developed. An equimolar catalytic mixture of tetra-n-butylammonium bromide and sodium nitrite catalyzes the aerobic selective oxidation of benzylic alcohols under oxidant-free, base-free and metal-free conditions. The mild reaction conditions allow oxidation of a wide range of benzylic alcohols, chemo-selectively to their carbonyl compounds (68-93% isolated yields). More importantly, high selectivity among different kinds of alcohols (aromatic vs. aliphatic alcohols, primary vs. secondary alcohols as well as alcohols having neutral rings vs. electron-deficient rings) is available by this approach. The method surprisingly switched over to be an efficient acetylation approach in the case of aliphatic alcohols without the use of any transition metal, phosphorous or other toxic reagents or any need for using toxic acyl halides, sulfonyl halides, anhydrides, etc. by the use of only acetic acid as a reagent.
Bismuth (III) nitrate supported onto silica gel, a new catalyst for acetylation of alcohols and phenols under microwave irradiation
Asadolah, Karim,Heravi, Majid M.
, p. 2335 - 2339 (2004)
Bismuth (III) nitrate supported onto silica gel is found to be efficient catalyst for acetylation of alcohols, phenols and naphthals in the presence of acetic anhydride under microwave irradiation in solventless system.
PALLADIUM-CATALYZED ALLYLIC OXIDATION OF OLEFINS BY t-BUTYL HYDROPEROXIDE AND TELLURIUM(IV) OXIDE
Uemura, Sakae,Fukuzawa, Shin-ichi,Toshimitsu, Akio,Okano, Masaya
, p. 87 - 90 (1982)
Treatment of several cyclic olefins, β-pinene, allylbenzene and estragole with palladium(II) salt in acetic acid in the presence of t-butyl hydroperoxide and tellurium(IV) oxide afforded mainly the corresponding allylic acetates.The reaction proceeded catalytically with palladium(II) salt, t-BuOOH working as a reoxidazing agent.
[BF4]: Silver-free and acid-free catalysts for water-inclusive gold-mediated organic transformations
Gomez-Suarez, Adrian,Oonishi, Yoshihiro,Meiries, Sebastien,Nolan, Steven P.
, p. 1106 - 1111 (2013)
The synthesis of a series of digold hydroxide complexes is reported. These diaurated species, of the formula [{Au(NHC)}2(μ-OH)][BF 4] (where NHC = IPrCl, IPr, IPent), were easily prepared via the cationic species [Au(NHC)(NCCH3)][BF4] in aqueous media. The catalytic activity of these novel complexes was tested and compared to that of the previously reported IPr and SIPr derivatives. These digold hydroxide species are highly active in water-inclusive organic transformations, such as the alkyne and nitrile hydration reactions, and the Meyer-Schuster rearrangement. One salient feature of these systems is the lack of any additive to induce catalytic activity.
