57440-42-3Relevant academic research and scientific papers
Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids
Senaweera, Sameera,Cartwright, Kaitie C.,Tunge, Jon A.
, p. 12553 - 12561 (2019/10/14)
Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C-O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu(OAc)2
Pummerer reaction of sulfoxides in acetic anhydride catalyzed by Al-MCM-41
Ito, Suguru,Kubota, Yoshihiro,Asami, Masatoshi
, p. 16 - 18 (2016/01/20)
The Pummerer reaction of acetic anhydride with both alkyl aryl sulfoxides and dialkyl sulfoxides was efficiently promoted by a mesoporous aluminosilicate Al-MCM-41 to afford the corresponding α-acetoxy sulfides in high yields. The catalyst was easily reco
Electrochemical Properties and Reactions of Sulfur-Containing Organoboron Compounds
Tanigawa, Masahiro,Kuriyama, Yu,Inagi, Shinsuke,Fuchigami, Toshio
, p. 314 - 318 (2016/04/26)
Electrochemical analyses of 4,4,5,5-tetramethyl-2-phenylsulfanylmethyl-[1,3,2]dioxaborolane and tetra-n-butylammonium phenylthiomethyltrifluoroborate were comparatively studied by cyclic voltammetry measurements and we found for the first time the β-effect of organoborate, which was indicated by experimental and theoretical aspects. The organoborate was found to have a much lower oxidation potential compared to the organoborane. Anodic substitution reaction of organoboronate ester and organoborate was successfully carried out in the presence of nucleophiles to afford the selectively substituted products in good yields.
Gold-Catalyzed, Iodine(III)-Mediated Direct Acyloxylation of the Unactivated C(sp3)–H Bonds of Methyl Sulfides
Guo, Sheng-rong,Santhosh Kumar, Pailla,Yuan, Yan-qin,Yang, Ming-hua
supporting information, p. 4260 - 4264 (2016/09/14)
The gold-catalyzed, iodine(III)-mediated direct oxidative acyloxylation of the C(sp3)–H bonds of methyl sulfides for the synthesis of various α-thioaryl and α-thioalkyl ester derivatives was discovered. Bis(acyloxy)iodobenzene proved to be an efficient reagent to activate the sulfur atom as an in situ directing group for α-C(sp3)–H functionalization. The attractive features of this protocol include short reaction times, low catalyst loading, and in situ activation of adjacent C(sp3)–H bonds of the sulfur atom.
Direct α-acyloxylation of organic sulfides with the hypervalent (diacyloxyiodo)benzene/tetra-n-butylammonium bromide (TBAB) reagent combination
Zhu, Dan,Chang, Denghu,Gan, Shaoyan,Shi, Lei
, p. 27983 - 27987 (2016/04/04)
A novel metal-free approach to directly synthesize α-acyloxy sulfides from readily available alkyl sulfides utilizing the hypervalent (diacyloxyiodo)benzene and TBAB reagent combination is reported. This transformation is characterized by its broad substrate scope in moderate to excellent yields, convenient operating conditions and outstanding functional group tolerance.
Enzyme-promoted kinetic resolution of acetoxymethyl aryl sulfoxides
Kwiatkowska, Ma?gorzata,Janicki, Ignacy,Kie?basiński, Piotr
, p. 23 - 28 (2015/06/08)
A simple and efficient method of the synthesis of enantiomerically enriched, unknown acetoxymethyl aryl sulfoxides has been developed which is based on an enzyme-catalyzed hydrolysis of racemic substrates under the kinetic resolution conditions. The hydro
Tin-Pummerer rearrangement in the synthesis of O,S-acetal derivatives
Hatlelid, Jostein,Benneche, Tore,Undheim, Kjell
, p. 1092 - 1095 (2007/10/03)
α-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of α-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction. Acta Chemica Scandinavica 1997.
Anodic Oxidation of (Trimethylsilyl)methanes with ?-Electron Substituents in the Presence of Nucleophiles
Koizumi, Toshio,Fuchigami, Toshio,Nonaka, Tsutomu
, p. 219 - 225 (2007/10/02)
It was found that oxidation potentials of methanes with ?-electron substituents were decreased by introduction of a trimethylsilyl group.The anodic oxidation of benzyl-, allyl-, aryl(or alkyl)thiomethyl-, and aryloxymethyl-substituted trimethylsilanes smoothly proceeded in the presence of nucleophiles, e.g. alcohols and carboxylic acids, to eliminate the trimethylsilyl groups giving the corresponding alkoxylated and carboxylated products in moderate or high yields without full optimization of electrolytic conditions, while aminomethylsilanes did not undergo such a kind of anodic oxidation.
A Novel Synthesis of Phenylthiomethyl (PTM) Ethers and Esters by Anodic Oxidation of Phenyl Trimethylsilylmethyl Sulfide
Koizumi, Toshio,Fuchigami, Toshio,Nonaka, Tsutomu
, p. 1095 - 1096 (2007/10/02)
It was found that anodic oxidation of phenyl trimethylsilylmethyl sulfide in the presence of alcohols and carboxylic acids afforded various kinds of PTM ethers and esters, respectively, in good to reasonable yields.
COPPER INDUCED SOLVOLYSIS OF SULFUR COMPOUNDS
Uguen, D.
, p. 541 - 542 (2007/10/02)
The displacement of a phenylthio group by an acetate ion some allylic or α-alcoxy sulfides and thioacetals was cleanly performed by treating them with a mixture of copper powder and cupric acetate in acetic acid.
