112-31-2Relevant articles and documents
One-pot conversion of olefins to carbonyl compounds by hydroboration/NMO-TPAP oxidation
Yates, Matthew H.
, p. 2813 - 2816 (1997)
An efficient method to oxidize an olefin to the less substituted carbonyl compound is described. This new methodology utilizes borane dimethyl sulfide followed by tetrapropylammonium perruthenate N-methylmorpholine N-oxide to oxidize the resulting alkylborane.
A useful and catalytic method for protection of carbonyl compounds into the corresponding 1,3-oxathiolanes and deprotection to the parent carbonyl compounds
Mondal, Ejabul,Sahu, Priti Rani,Khan, Abu T.
, p. 463 - 467 (2002)
A wide variety of carbonyl compounds 1 can be easily protected to the corresponding 1,3-oxathiolanes 2 in good yields in the presence of catalytic amount of perchloric acid in dry CH2Cl2 at 0-5 °C. On the other hand, various 1,3-oxathiolanes 2 can be selectively deprotected to the parent carbonyl compounds 1 in very good yields by H2MoO4·H2O-H2O2 catalyzed oxidation of ammonium bromide in the presence of perchloric acid in CH2Cl2-H2O solvent system. Mild reaction condition, high selectivity, efficient and relatively good yields are some of the major advantages of the procedure.
Shimizu,Kuwajima
, p. 2801,2802 (1979)
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Schwager,Knifton
, p. 256,257, 258, 259, 260 (1976)
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Well-defined alkylpalladium complexes with pyridine-carboxylate ligands as catalysts for the aerobic oxidation of alcohols
Melero, Cristobal,Shishilov, Oleg N.,Alvarez, Eleuterio,Palma, Pilar,Campora, Juan
, p. 14087 - 14100 (2012)
Neophylpalladium complexes of the type [Pd(CH2CMe 2Ph)(N-O)(L)], where N-O is picolinate or a related bidentate, monoanionic ligand (6-methylpyridine-2-carboxylate, quinoline-2-carboxylate, 2-pyridylacetate or pyridine-2-sulfonate) and L is pyridine or a pyridine derivative, efficiently catalyze the oxidation of a range of aliphatic, benzylic and allylic alcohols with oxygen, without requiring any additives. A versatile method is described which allows the synthesis of the above-mentioned complexes with a minimum synthetic effort from readily available materials. Comparison of the rates of oxidation of 1-phenylethanol with different catalysts reveals the influence of the structure of the bidentate N-O chelate and the monodentate ligand L on the catalytic performance of these complexes. The Royal Society of Chemistry 2012.
TiO2-Photocatalyzed Epoxidation of 1-Decene by H2O2 under Visible Light
Ohno, Teruhisa,Masaki, Yuji,Hirayama, Seiko,Matsumura, Michio
, p. 163 - 168 (2001)
1-Decene was converted to 1,2-epoxydecane on UV-irradiated TiO2 powder using molecular oxygen as the oxygen source. Other main products were nonanal and 2-decanone. For anatase-form TiO2 powders, the reaction rate was hardly affected by addition of hydrogen peroxide to the solution. In contrast, for rutile-form TiO2 powders, the rate of epoxide generation was significantly increased by addition of hydrogen peroxide. In this case, the reaction occurred under visible light as well as UV light. The selectivity of the production of 1,2-epoxydecane was higher under visible light than under UV light. The conversion efficiency of an incident photon to 1,2-epoxydecane was about 2 percent when irradiated with visible light in the range 440-480 nm. UV-visible diffuse reflection spectroscopy, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy suggested the generation of a Ti-η2-peroxide on rutile TiO2 surface after treatment with hydrogen peroxide. The initial step of the reaction under visible light was attributed to a photochemical reaction of this peroxide with 1-decene.
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Lee et al.
, p. 751 (1973)
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Dodecacarbonyl triiron, an efficient catalyst for photochemical isomerization of unsaturated alcohols, ethers and ester to their corresponding carbonyl compounds, enol ethers and esters
Iranpoor, Nasser,Mottaghinejad, Enayatolah
, p. 399 - 404 (1992)
Photochemical isomerization of unsaturated alcohols to their corresponding saturated aldehydes and ketones can be carried out efficiently by irradiaton at wavelengths > 560 nm in n-hexane at 25-30 deg C in the presence of catalytic amounts of dodecacarbonyl triiron.Unsaturated ethers and esters are likewise converted into their corresponding enol ethers and esters in moderate to high yields.Results of the reactions of benzylideneacetoneiron tricarbonyl with unsaturated compounds support the previously postulated mechanism in which the Fe(CO)3 moiety is the active species in the catalyses of the carbon-carbon double bond migration.
Catalytic Effect of a BH3:N,N-Diethylaniline Complex in the Formation of Alkenyl Catecholboranes from Alk-1-ynes and Catecholborane
Suseela, Yantrapragada,Prasad, A. S. Bhanu,Periasamy, Mariappan
, p. 446 - 447 (1990)
Alkenyl catecholboranes are readily formed by the reaction of catecholborane and alk-1-ynes at 25 deg C, in the presence of 10 molpercent of a BH3:N,N-diethylaniline complex, via a hydroboration-alkenyl transfer mechanism.
DIBALH: From known fundamental to an unusual reaction; Chemoselective partial reduction of tertiary amides in the presence of esters
An, Duk Keun,Heo, Yu Jin,Jaladi, Ashok Kumar,Kim, Hyun Tae
, p. 33809 - 33813 (2021/12/09)
This study presents a quick and reliable approach to the chemoselective partial reduction of tertiary amides to aldehydes in the presence of readily reducible ester groups using commercial DIBALH reagent. Moreover, the developed method was also extended to multi-functional molecules bearing ester moieties, which were successfully chemoselectively reduced to the corresponding aldehydes. This journal is
Chemo- And regioselective hydroformylation of alkenes with CO2/H2over a bifunctional catalyst
Hua, Kaimin,Liu, Xiaofang,Wei, Baiyin,Shao, Zilong,Deng, Yuchao,Zhong, Liangshu,Wang, Hui,Sun, Yuhan
supporting information, p. 8040 - 8046 (2021/11/01)
As is well known, CO2 is an attractive renewable C1 resource and H2 is a cheap and clean reductant. Combining CO2 and H2 to prepare building blocks for high-value-added products is an attractive yet challenging topic in green chemistry. A general and selective rhodium-catalyzed hydroformylation of alkenes using CO2/H2 as a syngas surrogate is described here. With this protocol, the desired aldehydes can be obtained in up to 97% yield with 93/7 regioselectivity under mild reaction conditions (25 bar and 80 °C). The key to success is the use of a bifunctional Rh/PTA catalyst (PTA: 1,3,5-triaza-7-phosphaadamantane), which facilitates both CO2 hydrogenation and hydroformylation. Notably, monodentate PTA exhibited better activity and regioselectivity than common bidentate ligands, which might be ascribed to its built-in basic site and tris-chelated mode. Mechanistic studies indicate that the transformation proceeds through cascade steps, involving free HCOOH production through CO2 hydrogenation, fast release of CO, and rhodium-catalyzed conventional hydroformylation. Moreover, the unconventional hydroformylation pathway, in which HCOOAc acts as a direct C1 source, has also been proved to be feasible with superior regioselectivity to that of the CO pathway.