101395-49-7Relevant articles and documents
KI-catalyzed α-acyloxylation of acetone with carboxylic acids
Wu, Ya-Dong,Huang, Bei,Zhang, Yue-Xin,Wang, Xiao-Xu,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 5936 - 5939 (2016)
The KI-catalyzed reaction of acetone with aromatic carboxylic acids is achieved, leading to α-acyloxycarbonyl compounds in good to excellent yields under mild reaction conditions. The present method exhibits good functional-group compatibility. Notably, t
Polymer supported reagents: Facile synthesis of β-oxalkyl (acetonyl) esters of carboxylic acids
Salunkhe, Manikrao M.,Sande, Amirhamja R.,Kanade, Annappa S.,Wadgaonkar, Prakash P.
, p. 2885 - 2891 (1997)
β-Oxoalkyl (acetonyl) esters have been synthesised in high yields and in a state of purity by reaction of chloroacetone with insoluble polymer supported carboxylate ions at room temperature.
KI catalyzed C–H functionalization of acetone for the synthesis of 2-oxopropyl hetero-aromatic carboxylates
Zhou, Xiao-Yu,Chen, Xia,Liu, Hai-Long
, p. 1556 - 1563 (2021)
KI catalyzed C–H functionalization of acetone with hetero-aromatic carboxylic acids has been developed. With potassium iodide as catalyst and sodium chlorite as oxidant, cascade reaction including α-H electrophilic substitution of acetone and nucleophilic
Oxidative C-H Acyloxylation of Acetone with Carboxylic Acids under Iodine Catalysis
Zhou, Xiao-Yu,Chen, Xia
supporting information, p. 1654 - 1662 (2021/01/21)
Iodine-catalyzed oxidative C(sp 3)-H acyloxylation of acetone with carboxylic acids has been developed. The method employs iodide as catalyst and sodium chlorite as oxidant. Substituted benzoic acids, naphthoic acids and heteroaromatic carboxyl
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.
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.
TBAI/TBHP mediated oxidative cross coupling of ketones with phenols and carboxylic acids: Direct access to benzofurans
Santhosh Kumar,Ravikumar,Chinna Ashalu,Rajender Reddy
supporting information, p. 33 - 37 (2017/12/11)
TBAI/TBHP mediated oxidative cross coupling of phenols and carboxylic acids with ketones has been reported under metal-free, base free, solvent free conditions enabling environmentally benign synthesis of aryloxyketones, acyloxy ketones and benzofurans. Phenoxyketones and acyloxylcarbonyl compounds were synthesized in good to high yields, where as benzofurans were synthesized in moderate yields. This method is operationally simple, works under mild conditions, using commercially available as well as inexpensive TBAI and an oxidant TBHP.
Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer
Ma, Xiaoshen,Herzon, Seth B.
, p. 8673 - 8695 (2016/10/17)
Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including alkenyl halides, sulfides, triflates, and phosphonates and provides a mild and practical alternative to the Tamao-Fleming oxidation of vinylsilanes and the Arndt-Eistert homologation.
A method for the selective hydrogenation of alkenyl halides to alkyl halides
King, Sandra M.,Ma, Xiaoshen,Herzon, Seth B.
, p. 6884 - 6887 (2014/06/09)
A general method for the selective hydrogenation of alkenyl halides to alkyl halides is described. Fluoro, chloro, bromo, iodo, and gem-dihaloalkenes are viable substrates for the transformation. The selectivity of the hydrogenation is consistent with reduction by a hydrogen atom transfer pathway.
Cyclization of alkynyl benzoates and generation of dioxolenylium ions
Allen, Annette D.,Kitamura, Tsugio,McClelland,Stang, Peter J.,Tidwell, Thomas T.
, p. 8873 - 8878 (2007/10/02)
Reactions of l-ethynyl benzoates RC≡CO2CC6H4X in H2O and CH3OH have been studied. In neutral H2O, reaction rates for CH3C≡CO2CC6H4X depend on σp of X with p of 1.3. Reaction of CH3C≡CO2CPh (1) in 18O-labeled H2O gives CH3CH2CO2H and PhCO2H in 54% relative yield with 90 and 83%, respectively, incorporation of a single 18O in the acids and CH3COCH2O2CPh (2) in 46% relative yield with 100% incorporation of 18O in both carbonyl oxygens. These results arc explained by the hypothesis that at least 46% of 1 reacts by cyclization to an intermediate 2-hydroxy-1,3-dioxolene 18. Mcthanolysis of 1 and other alkynyl benzoates gives 2-methoxy-1,3-dioxolenes, confirming the cyclization pathway. Reaction in 44% H2SO4 of 2-methoxy-2-phenyl-4-tert-butyl-1,3-dioxol-4-ene (8), prepared in this way, gives the 2-phenyl-4-tert-butyl-1,3-dioxol-4-enylium cation (16), directly observable by UV, which hydrolyzes to t-BuCOCH2O2CPh (12).
