130200-27-0Relevant academic research and scientific papers
Mild Halogenation of Stabilized Ester Enolates by Cupric Halides
Shi, Xiao-Xin,Dai, Li Xin
, p. 4596 - 4598 (1993)
The reactions of various stabilized ester enolates of 2-keto, 2-(alkoxycarbonyl), 2-phosphoryl, and 2-(benzenesulfonyl) esters with cupric chloride or cupric bromide have been examined.The reactions lead to 2-halo esters in good to excellent yields under mild condition.Enolates which contain an unsaturated functionality such as a double bond, a triple bond, or an allylic or a benzylic moiety react with high chemoselectivity.
Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids
Yang, Dan,Yan, Yi-Long,Lui, Bob
, p. 7429 - 7431 (2002)
Lewis acid Mg(ClO4)2, combined with NBS, in CH3CN or EtOAc provided mild and fast bromination of 1,3-dicarbonyl compounds. In particular, this protocol could be applied to the α-monobromination of α-unsubstituted β-keto es
Lanthanide-catalyzed oxyfunctionalization of 1,3-diketones, acetoacetic esters, and malonates by oxidative C-O coupling with malonyl peroxides
Terent'ev, Alexander O.,Vil', Vera A.,Gorlov, Evgenii S.,Nikishin, Gennady I.,Pivnitsky, Kasimir K.,Adam, Waldemar
, p. 810 - 823 (2016/02/18)
The lanthanide-catalyzed oxidative C-O coupling of 1,3-dicarbonyl compounds with diacyl peroxides, specifically the cyclic malonyl peroxides, has been developed. An important feature of this new reaction concerns the advantageous role of the peroxide acti
Mild and efficient α-chlorination of carbonyl compounds using ammonium chloride and oxone (2KHSO5·KHSO4· K2SO4)
Swamy, Peraka,Kumar, MacHarla Arun,Reddy, Marri Mahender,Narender, Nama
supporting information; experimental part, p. 432 - 434 (2012/06/01)
A simple protocol for the α-monochlorination of ketones and 1,3-dicarbonyl compounds utilizing NH4Cl as a source of chlorine and Oxone as an oxidant in methanol without catalyst is presented. The reaction proceeds at ambient temperature in yields ranging from moderate to excellent.
Enantioselective halogenation of β-oxo esters catalyzed by a chiral sulfoximine-copper complex
Frings, Marcus,Bolm, Carsten
supporting information; experimental part, p. 4085 - 4090 (2009/12/26)
A C1-symmetric amino sulfoximine has been used as a chiral ligand in copper-catalyzed asymmetric halogenation reactions of β-oxo esters. Both the catalyst itself and the reaction conditions were optimized, and 26 fluorinated, chlorinated, and b
Iron-catalyzed hydroxylation of β-ketoesters with hydrogen peroxide as oxidant
Li, Dongmei,Schr?der, Kristin,Bitterlich, Bianca,Tse, Man Kin,Beller, Matthias
scheme or table, p. 5976 - 5979 (2009/04/11)
The hydroxylation of β-ketoesters was studied using simple iron catalysts and 30 wt % hydrogen peroxide as the terminal oxidant. The highest activity and yield were achieved in the presence of iron(III) chloride. Cyclic β-ketoesters could be smoothly hydr
Rapid and catalyst-free α-halogenation of ketones using N-halosuccinamides in DMSO
Sreedhar,Reddy, P. Surendra,Madhavi
, p. 4149 - 4156 (2008/03/13)
α-Halogenation of various carbonyl compounds such as β-keto-esters, cyclic ketones, and lactams with N-halosuccinamides (NBS, NCS, NIS) in the presence of DMSO proceeded very smoothly to give the corresponding α-monohalogenated products in good to excellent yields with high selectivity under catalyst-free conditions. Copyright Taylor & Francis Group, LLC.
A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids
Meshram,Reddy,Vishnu,Sadashiv,Yadav
, p. 991 - 995 (2007/10/03)
Room temperature ionic liquids (ILs) are used as a green recyclable reaction media for the α-monohalogenation of 1,3-diketones, β-keto-esters and cyclic ketones with N-halosuccinimides in excellent yields in the absence of a catalyst. The recovered ionic liquid was reused five to six times with consistent activity.
Preparation of acyloins by cerium-catalyzed, direct hydroxylation of β-dicarbonyl compounds with molecular oxygen
Christoffers, Jens,Werner, Thomas,Unger, Sven,Frey, Wolfgang
, p. 425 - 431 (2007/10/03)
We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a-4i give high yields of analytically pure products 5a-5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j-4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j-5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
