14904-52-0Relevant academic research and scientific papers
An efficient method for the α-acetoxylation of ketones
Sheng, Jinmei,Li, Xiaolong,Tang, Mingfang,Gao, Botao,Huang, Guosheng
, p. 1165 - 1168 (2007)
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
Preparation method of alpha-acyloxy ketone compound
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Paragraph 0060-0062, (2021/08/06)
The invention discloses a preparation method of an alpha-acyloxy ketone compound, which comprises the following steps of adding a 1, 3-dicarbonyl compound, carboxylate and a catalyst alkyl halide into an organic solvent, and stirring and reacting for 0.5-1 hour at the temperature of 20-30 DEG C to obtain a reaction product, namely a mixture, performing purification treatment on the mixture to obtain alpha-acyloxy ketone, wherein the molar ratio of the 1, 3-dicarbonyl compound to the carboxylate to the alkyl halide is 1: 1: 1. According to the method, carboxylate with low cost is selected as an acyloxylation reagent, reaction conditions are mild and green, a 1, 3-dicarbonyl compound is taken as a raw material, and a novel method for efficiently, simply and conveniently constructing a C-O bond is successfully realized through activation of a carbonyl alpha-position C-H bond and subsequent cascade reaction, so that a series of alpha-acyloxyketone compounds are obtained.
Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
Bityukov, Oleg V.,Matveeva, Olesya K.,Vil, Vera A.,Kokorekin, Vladimir A.,Nikishin, Gennady I.,Terent'Ev, Alexander O.
, p. 1448 - 1460 (2019/02/07)
The electrochemically induced cross-dehydrogenative C-O coupling of β-diketones and β-ketoesters (C-H reagents) with carboxylic acids (O-H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C-O
Rhodium-Catalyzed Synthesis of Sulfur Ylides via in Situ Generated Iodonium Ylides
Vaitla, Janakiram,Hopmann, Kathrin H.,Bayer, Annette
supporting information, p. 6688 - 6691 (2017/12/26)
A convenient strategy for the synthesis of sulfur ylides via rhodium-catalyzed coupling of in situ generated iodonium ylides with sulfides or sulfoxides has been developed. A wide range of sulfur ylides were obtained in moderate to good yields from inexpensive sulfur compounds and active methylene compounds with a short reaction time (MW, 5-10 min) or 12-16 h at rt. Furthermore, these sulfoxonium ylides were used as novel acceptor/acceptor carbenes for N-H insertion reactions.
PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones
Chen, Ming,Zhang, Wei,Ren, Zhi-Hui,Gao, Wen-Yun,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 761 - 768 (2017/06/05)
Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.
Preparation of iodonium ylides: Probing the fluorination of 1,3-dicarbonyl compounds with a fluoroiodane
Geary, Gemma C.,Hope, Eric G.,Singh, Kuldip,Stuart, Alison M.
, p. 16501 - 16506 (2015/03/04)
The isolation of iodonium ylide 8, from the reaction of fluoroiodane 1 with ethyl 3-oxo-3-phenylpropanoate 5 in the presence of potassium fluoride, provides strong evidence that 1,3-dicarbonyl compounds undergo an addition reaction with fluoroiodane 1 to form an iodonium intermediate which can be deprotonated to generate an iodonium ylide. In the presence of TREAT-HF, however, the iodonium intermediate reacts to form the 2-fluoro-1,3-dicarbonyl product and we propose that fluoroiodane 1 simulates electrophilic fluorination via an addition/substitution mechanism. Further evidence to support this mechanism was obtained by successfully reacting the isolated iodonium ylide 8 with TREAT-HF, hydrochloric acid, acetic acid and p-toluenesulfonic acid to form the 2-fluoro-, 2-chloro-, 2-acetyl- and 2-tosyl-1,3-ketoesters respectively. This journal is
A copper-catalyzed formal O-H insertion reaction of α-diazo-1,3- dicarbonyl compounds to carboxylic acids with the assistance of isocyanide
Wang, Zikun,Bi, Xihe,Liang, Yongjiu,Liao, Peiqiu,Dong, Dewen
supporting information, p. 3976 - 3978 (2014/04/03)
A novel copper-catalyzed formal O-H insertion of α-diazo-1,3- dicarbonyl compounds to carboxylic acids has been developed, providing a straightforward synthetic method for α-acyloxy-1,3-dicarbonyl compounds, in which the activation of carboxylic acids by isocyanide plays a crucial role.
Facile synthesis of 2-fluoro-1,3-dicarbonyl compounds with aqueous hydrofluoric acid mediated by iodosylarenes
Kitamura, Tsugio,Kuriki, Satoshi,Muta, Kensuke,Morshed, Mohammad Hasan,Muta, Kazutaka,Gondo, Keisuke,Hori, Yuji,Miyazaki, Masaya
, p. 3125 - 3130 (2013/12/04)
Direct fluorination of 1,3-dicarbonyl compounds including 1,3-diketones, 3-oxo esters, and 3-oxoamides was conducted using aqueous hydrofluoric acid with the aid of iodosylarenes, giving the corresponding 2-fluorinated products in good to high yields. Among the used iodosylarenes, o-iodosyltoluene was found to be the most effective, and the yield of 2-fluorinated products was improved. Georg Thieme Verlag Stuttgart New York.
TBAI-catalyzed oxidative coupling of β-ketoesters with carboxylic acid: Synthesis of α-carboxylic-β-ketoesters
Li, Xiaoqing,Zhou, Can,Xu, Xiangsheng
, p. 150 - 158 (2013/01/16)
TBAI-catalyzed oxidative coupling of β-ketoesters with carboxylic acid using TBHP as oxidant has been established. This transformation provides a facile and direct strategy for the synthesis of α-carboxylic-β- ketoesters. ARKAT-USA, Inc.
Highly diastereoselective and enantioselective synthesis of α-hydroxy β-amino acid derivatives: Lewis base catalyzed hydrosilylation of α-acetoxy β-enamino esters
Jiang, Yan,Chen, Xing,Zheng, Yongsheng,Xue, Zhouyang,Shu, Chang,Yuan, Weicheng,Zhang, Xiaomei
, p. 7304 - 7307 (2011/09/16)
By design: A series of α-acetoxy-β-enamino esters 1 were synthesized and then subjected to catalytic asymmetric hydrosilylation. In the presence of a chiral Lewis base catalyst, the reactions proceeded smoothly to provide a wide range of chiral α-acetoxy β-amino acid derivatives in high yields with good diastereoselectivities and enantioselectivities. Copyright
