7472-23-3Relevant academic research and scientific papers
Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
Doiuchi, Daiki,Uchida, Tatsuya
supporting information, p. 7301 - 7305 (2021/10/01)
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.
1,2-Dibromoethane and KI mediated α-acyloxylation of ketones with carboxylic acids
Wang, Xujie,Li, Gangsheng,Yang, Yanan,Jiang, Jianshuang,Feng, Ziming,Zhang, Peicheng
supporting information, p. 711 - 714 (2019/09/30)
The 1,2-dibromoethane- and KI-mediated α-acyloxylation of ketones is reported in moderate to good yield without the use of transition metals and strong oxidants. Various acids are well tolerated with wide functional group compatibility. An 1,2-dibromoethane- and KI-catalysed reaction mechanism is proposed based on the results of control experiments.
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.
Catalytic Enantioselective α-Ketol Rearrangement
Wu, Hua,Andres, Rémi,Wang, Qian,Zhu, Jieping
, p. 499 - 503 (2018/12/13)
A highly enantioselective α-ketol rearrangement has been developed. In the presence of a chiral Cu-bisoxazoline complex, achiral β-hydroxy-α-dicarbonyls were isomerized to chiral α-hydroxy-β-dicarbonyls and their bicyclic derivatives in excellent yields and enantioselectivities. Enantioenriched 2-acyl-2-hydroxy cyclohexan-1-ones, dihydroxyhexahydrobenzofuranones, and dihydroxyhexahydro-cycloheptafuranones, with up to three stereocenters, were readily prepared from achiral starting materials in one operation. The reaction is applicable to the desymmetrization of meso substrates and kinetic resolution of racemic alcohols.
C–O bond formation via oxidative-coupling pathway in eutectic mixture of choline chloride/urea as a green solvent
Saberi, Dariush,Manouchehri, Neda,Niknam, Khodabakhsh
, p. 680 - 687 (2019/01/03)
C–O bond formation between terminal alkenes/benzyl alcohols as an arylcarboxy surrogate and carbonyl compounds in a biodegradable deep eutectic solvent (DES) based on choline chloride and urea was performed. By employment of TBAI as catalyst and TBHP as oxidant, various derivatives of carbonyl compounds were benzylated in α position in good to high yield at 90 °C. Moreover, α-oxybenzoylation of diethyl malonate with carboxylic acids was performed in the above-mentioned DES by employment of NaI as the catalyst and TBHP as the oxidant at 60 °C.
Copper-catalyzed α-C-H acyloxylation of carbonyl compounds with terminal alkynes
Li, Jiao,Yang, Zan,Yang, Tao,Yi, Jianmin,Zhou, Congshan
supporting information, p. 1581 - 1584 (2018/02/09)
Herein, a copper/TBHP catalyst system for the α-C-H acyloxylation of carbonyl compounds is developed using terminal alkynes as the acyloxy source. A variety of carbonyl compounds and terminal alkynes are tolerated in this reaction. In addition, its possible mechanism is proposed.
Method for preparing alpha-acyloxy ketone compound from terminal alkyne compounds
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Paragraph 0042, (2017/09/01)
The invention provides a method for efficiently synthesizing an alpha-acyloxy ketone compound containing different substitute functional groups. According to the method, acetylacetone copper is taken as a reaction catalyst, t-butylhydroperoxide is taken as an antioxidant, ketone compounds and terminal alkyne compounds are taken as reaction substrates, and an organic solvent is added into a reaction system. The method has the advantages that the catalyst is cheap and easily available; reaction conditions are mild, safe and reliable; and the productivity of an obtained target product is relatively high. According to the method, the problem that a traditional alpha-acyloxylation reaction system is single is solved, and a novel acyloxylation reagent is provided; and the method has good industrial application prospects.
Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
Kroc, Michelle A.,Patil, Aditi,Carlos, Anthony,Ballantine, Josiah,Aguilar, Stephanie,Mo, Dong-Liang,Wang, Heng-Yen,Mueller, Daniel S.,Wink, Donald J.,Anderson, Laura L.
, p. 4125 - 4137 (2017/06/29)
A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.
Bu4NI-Catalyzed α-Oxyacylation of Carbonyl Compounds with Toluene Derivatives
Li, Chengliang,Jin, Tao,Zhang, Xinglu,Li, Chunju,Jia, Xueshun,Li, Jian
supporting information, p. 1916 - 1919 (2016/05/19)
A TBAI (tetrabutylammonium iodide)-catalyzed direct α-oxyacylation of carbonyl compounds from readily available toluene derivatives has been developed. The distinguished features of this metal-free protocol include the employment of simple starting material, a wide carbonyl compound scope, and mild reaction conditions.
Sequential [3,3]-Sigmatropic Rearrangement/Nucleophilic Arylation of N -(Benzoyloxy)enamides towards the Preparation of Cyclic β-Aryl-β-amino Alcohols
Sato, Shohei,Takeda, Norihiko,Ueda, Masafumi,Miyata, Okiko
, p. 882 - 892 (2016/03/15)
A new method has been developed for the efficient synthesis of cyclic β-aryl-β-amino alcohol derivatives bearing a tetrasubstituted carbon center via the [3,3]-sigmatropic rearrangement of N-(benzoyl oxy)enamides followed by nucleophilic arylation reactio
