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103-79-7Relevant articles and documents
Ferrous Ion Catalysis of Reactions of Nucleophiles with Aryl Halides
Galli, Carlo,Bunnett, J. F.
, p. 3041 - 3042 (1984)
Reactions of ketone enolate ions and of diethyl phosphite ion with bromo- and iodobenzene in ammonia or dimethyl sulfoxide solution occur in preparatively useful amounts under catalysis by iron(II) salts, apparently via the SRN1 mechanism.
A NEW PALLADIUM CATALYZED AROMATIC ACETONYLATION BY ACETONYLTRIBUTYLTIN
Kosugi, Masanori,Suzuki, Mikio,Hagiwara, Isao,Goto, Katsuhisa,Saitoh, Kyoko,et al.
, p. 939 - 940 (1982)
The reaction of acetonyltributyltin, prepared from tributyltin methoxide and isopropenyl acetate in situ, with aryl bromide in the presence of a catalytic amount of PdCl2(o-tolyl3P)2 was found to give arylacetones in good yields.
Developing backbone-modified Mor-DalPhos ligand variants for use in palladium-catalyzed C-N and C-C cross-coupling
MacLean, Mark A.,Wheaton, Craig A.,Stradiotto, Mark
, p. 712 - 721 (2018)
The present contribution describes the systematic structural diversification of the ?°2-P,N DalPhos ligand family in an effort to improve catalytic efficiency in the monoarylation of ammonia and acetone. The study is focused primarily on modifying the backbone phenylene linker, while retaining the same bite angle and steric bulk as the Mor-DalPhos ligand through the use of P(1-Ad)2 and morpholine donors. Eight new variants of Mor-DalPhos were prepared; two of these feature a pyridine linker (L1, L2), and five others feature either electron-donating (L3, L4) or electron-withdrawing (L5-L7) substituents on the phenylene linker. Additionally, thiomorpholino substitution (L8) was performed to investigate the effects of a possible tridentate coordination mode. Precatalyst complexes of the general formula LPd(cinnamyl)Cl were prepared and characterized in both solution and solid state. Solution studies demonstrated a significant degree of lability in the Pd-N bond, whereby dynamic behavior is seen to be dependent on the nature of the ligand backbone. The utility of these new ligands in the palladium-catalyzed monoarylation of ammonia or acetone was then surveyed. Notably, pyridine-derived ligand variants (L1, L2) were observed to out-perform parent Mor-DalPhos in the latter transformations.
A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids
Zhao, Mangzhu,Li, Jing,Song, Zhiguo,Desmond, Richard,Tschaen, David M.,Grabowski, Edward J. J.,Reider, Paul J.
, p. 5323 - 5326 (1998)
A novel CrO3 catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of H3IO6 in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.
Hydration and alkoxylation of alkynes catalyzed by NHC-Au-OTf
Gatto, Mattia,Baratta, Walter,Belanzoni, Paola,Belpassi, Leonardo,Del Zotto, Alessandro,Tarantelli, Francesco,Zuccaccia, Daniele
, p. 2125 - 2134 (2018)
The NHC-Au-OTf [NHC = 1,3-bis(2,6-di-isopropylphenyl)-imidazol-2-ylidene] catalyst was tested in the alkoxylation and hydration of alkynes in a wide set of neoteric solvents for the first time. We found that most of these solvents (ethyl lactate, glycerol, propylene carbonate, d-limonene, γ-valerolactone, and p-cymene) are comparable or better solvents with respect to traditional VOSs. An important beneficial effect of γ-valerolactone was found in the hydration of inactive diphenylacetylene and one order of magnitude higher TOF was obtained with respect to the literature values. Kinetic experiments and DFT calculations seem to indicate that the polarity of the solvent and the presence of suitable proton acceptor/donor functionalities on the solvent itself could be taken into account.
N,O-ligated Pd(ii) complexes for catalytic alcohol oxidation
Dornan, Laura M.,Clendenning, Grainne M. A.,Pitak, Mateusz B.,Coles, Simon J.,Muldoon, Mark J.
, p. 2526 - 2534 (2014)
N,O-ligated Pd(ii) complexes show considerable promise for the oxidation of challenging secondary aliphatic alcohols. The crystal structures of the highly active complexes containing the 8-hydroxyquinoline-2-carboxylic acid (HCA) and 8-hydroxyquinoline-2-sulfonic acid (HSA) ligands have been obtained. The (HSA)Pd(OAc)2 system can effectively oxidise a range of secondary alcohols, including unactivated alcohols, within 4-6 h using loadings of 0.5 mol%, while lower loadings (0.2 mol%) can be employed with extended reaction times. The influence of reaction conditions on catalyst degradation was also examined in these studies.
One-pot oxidation of aromatic and cyclic hydrocarbons using the Au (III) and Pd (II) catalyst under microwave irradiation
Srivastava, Manish,Srivastava, Anamika,Goyal, Ashu,Mishra, Aakanksha,Tomer, Preeti,Dwivedi, Jaya,Kishore
, (2017)
We report here in highly efficient one-pot catalytic system which utilizes in situ generated sodium ferrate for the oxidation of aromatic and cyclic hydrocarbons in the presence of Au (III) and Pd (II) metal ions catalyst under ecofriendly green synthetic method. Results of these studies revealed that Au (III) catalytic system gave higher yield as compared with Pd (II) catalytic system because of the higher electrode potential of Au(III) than Pd(II). All compounds were characterized by infrared and NMR spectral analysis. Copyright
Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones
Anderson, Andrew M.,Blazek, Jesse M.,Garg, Parie,Payne, Brian J.,Mohan, Ram S.
, p. 1527 - 1530 (2000)
Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement in the presence of 10-50 mol% bismuth(III) oxide perchlorate, BiOClO4·XH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C-O bond is formed. BiOClO4·XH2O is relatively non-toxic, insensitive to air and inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3·Et2O or INCl3 currently used to effect epoxide rearrangements. (C) 2000 Elsevier Science Ltd.
A recyclable catalytic system based on a temperature-responsive catalyst
Hamamoto, Hiromi,Suzuki, Yachiyo,Yamada, Yoichi M. A.,Tabata, Hidetsugu,Takahashi, Hideyo,Ikegami, Shiro
, p. 4536 - 4538 (2005)
(Figure Presented) A new concept for catalytic reactions in aqueous media is demonstrated by using a temperature-responsive polymer support, poly(N-alkylacrylamide), which is converted into a catalyst by assembly with phosphotungstic acid. At high temperature, the catalyst is highly active in the oxidation of alcohols with H2O2 owing to the formation of emulsions, whereas the product and catalyst are easily separated at low temperature (see scheme).
Alcohol oxidation via recyclable hydrophobic ionic liquid-supported IBX
Koguchi, Shinichi,Mihoya, Aya,Mimura, Minato
, p. 7633 - 7637 (2016)
The first ionic hydrophobic liquid-supported 1-hydroxy-1,2-benziodoxole-3(1H)-one-1-oxide (IBX) reagent was prepared for oxidizing alcohols. In this study, a hydrophobic ionic liquid-supported IBX reagent was synthesized and described. This hydrophobic ionic liquid-supported IBX reagent was able to be recovered and used in a recyclable reaction system by re-oxidation and washing.