30076-98-3Relevant academic research and scientific papers
Enantioselective Flow Synthesis of Rolipram Enabled by a Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using in Situ-Generated Persulfuric Acid as Oxidant
Nagy, Bence S.,Llanes, Patricia,Pericas, Miquel A.,Kappe, C. Oliver,?tv?s, Sándor B.
supporting information, (2022/02/05)
A novel approach is reported for the enantioselective flow synthesis of rolipram comprising a telescoped asymmetric conjugate addition-oxidative aldehyde esterification sequence followed by trichlorosilane-mediated nitro group reduction and concomitant la
Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I
Cao, Fu-Rong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing
, (2021/06/21)
A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.
Photochemical synthesis of acetals utilizing Schreiner's thiourea as the catalyst
Kokotos, Christoforos G.,Nikitas, Nikolaos F.,Spiliopoulou, Nikoleta
supporting information, p. 3539 - 3545 (2020/06/25)
Acetalization of aldehydes is an area of great importance in Organic Chemistry for both synthetic and biological puproses. Herein, we report a mild, inexpensive and green photochemical protocol, where Schreiner's thiourea (N,N′-bis[3,5-bis(trifluoromethyl)-phenyl]-thiourea) is utilized as the catalyst and cheap household lamps as the light source. A variety of aromatic and aliphatic aldehydes were converted into acetals in good to high yields (23 examples, 36-96% yield) and an example of the synthesis of a cyclic acetal is provided. The reaction mechanism was also studied.
Synthesis, structural determination and catalytic study of a new 2-D chloro-substituted zinc phosphate, (C8N2H20)[ZnCl(PO3(OH))]2
Rayes, Ali,Herrera, Raquel P,Moncer, Manel,Ara, Irene,Calestani, Gianluca,Ayed, Brahim,Mezzadri, Francesco
, (2019/11/03)
A novel chloro-substituted zinc-phosphate, (C8N2H20)[ZnCl(PO3(OH))], has been synthesized by a slow evaporation method in the presence of 1,3-cyclohexanebis- (methylamine), which acts as a template. The structure consists of vertex linked ZnO3Cl and PO3(OH) tetrahedral, assembled into corrugated porous layers [ZnCl(PO3(OH))2]∞ with (4.82) topology. The optical properties were also investigated using Diffuse Reflecting Spectroscopy (DRS), showing that the title compound has semiconducting properties. In addition, the catalytic activity of (C8N2H20)[ZnCl(PO3(OH))]2 has been tested in the acetalisation reaction of aldehydes. The title compound displayed a high catalytic activity with practically total conversion in many examples using MeOD as solvent and as the sole source of acetalisation. More importantly, the reaction crudes are very clean and only the preferred products are found in the NMR spectra.
Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
, (2020/01/13)
Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
Photo-organocatalytic synthesis of acetals from aldehydes
Nikitas, Nikolaos F.,Triandafillidi, Ierasia,Kokotos, Christoforos G.
supporting information, p. 669 - 674 (2019/02/14)
A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.
Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions
Subaramanian, Murugan,Landge, Vinod G.,Mondal, Akash,Gupta, Virendrakumar,Balaraman, Ekambaram
supporting information, p. 4557 - 4562 (2019/08/30)
A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.
Synthesis of propargylic ethers by gold-mediated reaction of terminal alkynes with acetals
Furuta, Miyu,Sugiyama, Kyoko,Yamaguchi, Minami,Ueda, Hirofumi,Tokuyama, Hidetoshi
, p. 872 - 876 (2019/08/20)
A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.
House bulb light-induced photochemical acetalization of carbonyl compounds catalyzed by Eosin Y
Zhou, Quan,Jia, Tao,Li, Xiao-Xuan,Zhou, Lin,Li, Chang-Jiang,Feng, Yi-Si
supporting information, p. 1068 - 1075 (2018/05/23)
We have systematically studied the reactions of acetalization and found that high reaction efficiency can be achieved using cheap and readily available organic Eosin Y as catalyst. The reaction proceeds smoothly under house bulbs and shows excellent functional group tolerance. The substrates of the reaction system are compatible with aromatic aldehydes, aliphatic aldehydes, aromatic ketones, and cyclic ketones with high yields.
Hydrothermal synthesis of chiral inorganic-organic CoII complex: Structural, thermal and catalytic evaluation
Salah, Assila Maatar Ben,Herrera, Raquel P.,Na?li, Houcine
, p. 356 - 362 (2018/05/29)
By heating the cobalt chloride hexahydrate (CoCl2·6H2O) with the R form of the organic amine α-methylbenzylamine (C8H11N) under hydro(solvo)thermal conditions, we have successfully generated the corresponding non-centrosymmetric homochiral hybrid tris (α-methylbenzylammonium tetrachloridocobaltate chloride [R-(C8H12N)3][CoCl4]Cl abbreviated R(MBA)Co. We present the growth conditions together with a characterization of the single crystals by means of X-ray single-crystal diffraction, Fourier-transform infrared, TG/TDA thermal decomposition and catalytic properties. This inorganic–organic hybrid compound crystallizes in the chiral space group P21 and exhibits a supramolecular-layered organization wherein a double layer of (R)-methylbenzylammonium cations and the uncoordinated chloride anions are sandwiched between anionic layers, formed by isolated tetrachloridocobaltate tetrahedra. The crystal packing is governed by a three-dimensional network of N/C–H?Cl hydrogen bonds between the inorganic and organic moieties and C–H···π interactions between the aromatic rings of the organic moieties themselves. Thermal analysis discloses a phase transition at the temperature 130 °C. The Co complex was also employed as suitable catalyst activating the acetal formation reaction of aldehydes using MeOH as solvent and as the unique source of acetalization.
