17472-04-7Relevant academic research and scientific papers
Baeyer–Villiger Oxidation of Cyclohexanone by Hydrogen Peroxide with Fe3O4@GO as Catalyst Under Solvent Free Conditions
Xiao, Guansheng,Gao, Xi,Yan, Weiting,Wu, Tao,Peng, Xinhua
, (2019)
Abstract: An efficient magnetic nanocomposite catalyst (Fe3O4@GO) was synthesized and utilized as a sustainable and convenient catalyst for Baeyer–Villiger oxidation. The catalyst was characterized by XRD, FT-IR, TEM, SEM, XPS, Raman
3D-Network porous polymer bonded metalloporphyrin: An efficient and reusable catalyst for the Baeyer-Villiger oxidation
Hamid, Sheida,Mouradzadegun, Arash
, (2021/12/06)
A new, green catalyst was prepared through immobilization of metalloporphyrin on the surface of 3D-network polymer based on calix[4]resorcinarene (PC4RA), which efficiently catalyze B-V oxidation reaction using O2/benzaldehyde. The catalyst demonstrated excellent activity, which is highly potential for cyclic aliphatic ketones oxidation under mild conditions. IR spectroscopy, UV-Vis spectroscopy, thermal gravimetric analysis, energy dispersive spectroscopy and scanning electron microscopy are some of the spectroscopic methods used to characterize the new synthesized solid support.
Microwave-Enhanced Coupling of Carboxylic Acids with Liquid Ketones and Cyclic Ethers Using Tetrabutylammonium Iodide/ t-Butyl Hydroperoxide
Macías-Benítez, Pablo,Moreno-Dorado, F. Javier,Guerra, Francisco M.
, p. 6027 - 6043 (2020/05/22)
The oxidative coupling of carboxylic acids with liquid ketones and cyclic ethers has been accomplished in minutes using t-butyl hydroperoxide in the presence of tetrabutylammonium iodide under microwave irradiation in the absence of a solvent. In addition to drastically shortening the reaction times, the use of microwaves resulted, in general, in yields equal to or higher than those obtained by conventional heating.
Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes
Mikhael, Myriam,Adler, Sophia A.,Wengryniuk, Sarah E.
, p. 5889 - 5893 (2019/08/26)
The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ3-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial PhI(OAc)2 and can be either isolated or generated in situ. Conformational selectivity is demonstrated in both flexible 1,2-substituted cyclohexanols and rigid polyol scaffolds, providing chemists with a novel tool for chemoselective oxidation.
A Counterion-Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes
Kiss, Emily,Campbell, Craig D.,Driver, Russell W.,Jolliffe, John D.,Lang, Rosemary,Sergeieva, Tetiana,Okovytyy, Sergiy,Paton, Robert S.,Smith, Martin D.
supporting information, p. 13813 - 13817 (2016/10/26)
An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds
Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process
Zhou, Xiaoqiang,Ma, Haojie,Cao, Jinhui,Liu, Xingxing,Huang, Guosheng
supporting information, p. 10070 - 10073 (2016/11/06)
Hydrogen peroxide and anhydride mediated transformation of enamides to afford substituted α-acyloxy ketones is described. This transition-metal-free cascade reaction has a broad substrate scope and high efficiency. The acyl intramolecular migration procedure successfully achieved this acyloxylation process under mild conditions and increased the atom efficiency.
Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents
Mizar, Pushpak,Wirth, Thomas
, p. 5993 - 5997 (2014/06/10)
The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).
Silver acetate mediated acetoxylations of alkyl halides
Nolla-Saltiel, Roberto,Carrillo-Arcos, Ulises Alonso,Porcel, Susana
supporting information, p. 165 - 169 (2014/03/21)
Silver acetate promotes the acetoxylation of alkyl halides under neutral reaction conditions. The reaction is applicable to primary and activated secondary alkyl halides, and 2,2-dibromoacetophenones for preparing the corresponding acetates in good yields. The presence of ester, amide, nitrile, hydroxy, and OTBDMS functions on the substrate is tolerated.
A multicatalyst system for the one-pot desymmetrization/oxidation of meso-1,2-alkane diols
Mueller, Christian E.,Hrdina, Radim,Wende, Raffael C.,Schreiner, Peter R.
supporting information; experimental part, p. 6309 - 6314 (2011/08/07)
Two is better than one: We demonstrate the viability of an organocatalytic reaction sequence along a short peptide backbone that carries two independent catalytic functionalities, which allow the rapid, one-pot acylative desymmetrization and oxidation of meso-alkane-1,2-diols to the corresponding acetylated acetoins with good yields and enantioselectivities (see scheme). Copyright
An efficient method for the α-acetoxylation of ketones
Sheng, Jinmei,Li, Xiaolong,Tang, Mingfang,Gao, Botao,Huang, Guosheng
, p. 1165 - 1168 (2008/02/03)
α-Acetoxylation of ketones catalyzed by iodobenzene using 30% aqueous hydrogen peroxide and acetic anhydride as the oxidant is an effective and economical method for the preparation of a-acetoxy ketones. The reaction gave the products in good yields witho
