35010-24-3Relevant academic research and scientific papers
Photocatalytic Hydromethylation and Hydroalkylation of Olefins Enabled by Titanium Dioxide Mediated Decarboxylation
Zhu, Qilei,Nocera, Daniel G.
, p. 17913 - 17918 (2020/12/04)
A versatile method for the hydromethylation and hydroalkylation of alkenes at room temperature is achieved by using the photooxidative redox capacity of the valence band of anatase titanium dioxide (TiO2). Mechanistic studies support a radical-based mechanism involving the photoexcitation of TiO2 with 390 nm light in the presence of acetic acid and other carboxylic acids to generate methyl and alkyl radicals, respectively, without the need for stoichiometric base. This protocol is accepting of a broad scope of alkene and carboxylic acids, including challenging ones that produce highly reactive primary alkyl radicals and those containing functional groups that are susceptible to nucleophilic substitution such as alkyl halides. This methodology highlights the utility of using heterogeneous semiconductor photocatalysts such as TiO2 for promoting challenging organic syntheses that rely on highly reactive intermediates.
Rh(I)-catalyzed cross-coupling of α-diazoesters with arylsiloxanes
Xia, Ying,Liu, Zhen,Feng, Sheng,Ye, Fei,Zhang, Yan,Wang, Jianbo
supporting information, p. 956 - 959 (2015/03/30)
An Rh(I)-catalyzed cross-coupling of diazoesters with arylsiloxanes has been successfully achieved. This transformation is a new method for the construction of the C(sp3)-C(sp2) bond, thus providing an alternative synthesis of α-aryl esters. Rh(I)-carbene migratory insertion has been proposed to be involved in this coupling reaction. The reaction represents the first example of utilizing arylsiloxane as the coupling partner in the carbene-involved cross-coupling reactions.
Oxidative rearrangement of alkyl aryl/heteroaryl ketones by 1,2-aryl/heteroaryl shift using iodic acid
Huddar, Sameerana N.,Deshmukh, Swapnil S.,Akamanchi, Krishnacharya G.
experimental part, p. 67 - 75 (2011/06/19)
A method for synthesis of α-aryl/heteroaryl alkanoic acids involving oxidative rearrangement of alkyl aryl/heteroaryl ketones by 1,2-aryl/heteroaryl shift using iodic acid is described. ARKAT-USA, Inc.
3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 1: Discovery and exploration of the carboxyamide side chain
Asada, Masaki,Obitsu, Tetsuo,Nagase, Toshihiko,Tanaka, Motoyuki,Yamaura, Yoshiyuki,Takizawa, Hiroya,Yoshikawa, Ken,Sato, Kazutoyo,Narita, Masami,Ohuchida, Shuichi,Nakai, Hisao,Toda, Masaaki
experimental part, p. 80 - 90 (2010/04/05)
A series of 3-(2-aminocarbonyl-4-phenoxymethylphenyl)propanoic acid analogs were synthesized and evaluated for their EP3 antagonist activity in the presence of additive serum albumin. Several compounds were biologically evaluated for their in vivo efficacy with respect to the PGE2-induced uterine contraction in pregnant rats as well as their pharmacokinetics. The discovery process of these potent and selective EP3 antagonists and their structure activity relationship are also presented.
Synthesis of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives
Kulig,Ignasik,Malawska
experimental part, p. 1629 - 1636 (2010/07/06)
Syntheses of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives are described. The final compounds were obtained by the reductive cyclization of relevant cyanoalkanoate esters using NaBH4 and CoCl2.6H2O. The obtained pyrroIidin-2-one derivatives are pharmacophoric fragments for the synthesis of various biologically active compounds.
Arylation and vinylation of α-diazocarbonyl compounds with boroxines
Peng, Cheng,Zhang, Wei,Yan, Guobing,Wang, Jianbo
supporting information; experimental part, p. 1667 - 1670 (2009/08/07)
An alternative approach for α-arylation and α-vinylation of carbonyl compounds is described: reaction between aryl-or vinylboroxines with α-diazocarbonyl compounds leads to the formation of α-arylated or α-vinylated carbonyl compounds under mild conditions.
Direct competitive enzyme-linked immunosorbent assay for the determination of the highly polar short-chain sulfophenyl carboxylates
Estevez, M.-Carmen,Galve, Roger,Sanchez-Baeza, Francisco,Marco, M.-Pilar
, p. 5283 - 5293 (2008/02/02)
A direct enzyme-linked immunosorbent assay for the detection of the short-chain sulfophenylcarboxylic acids (SPCs), the main metabolites of the linear alkylbenzene-sulfonates, is reported. Six SPCs (2C3, 2C 4, 3C4, 2C
New oxidative transformations of alkenes and alkynes under the action of diacetoxyiodobenzene
Yusubov,Zholobova,Filimonova,Chi, Ki-Whan
, p. 1735 - 1742 (2007/10/03)
Treatment of alkenes and alkynes with diacetoxyiodobenzene activated by mineral and organic acids predominantly results in oxidative rearrangement. 1,4-Diphenylbutadiene in MeOH gives 3,4-dimethoxy-1,4-diphenylbut-1-ene.
A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions
Sarakinos, Georgios,Corey
, p. 1741 - 1744 (2008/02/11)
(formula presented) The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55°C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted to Z-polassium enolates and alkylated with high face selectivity.
Carbanion Rearrangements by Intramolecular 1,ω Proton Shifts, III. The Reaction of 2-, 3-, 4-, and 5-Phenylalkyllithium Compounds
Maercker, Adalbert,Passlack, Michael
, p. 540 - 577 (2007/10/02)
Upon addition of THF to a solution of 4-phenylbutyllithium (2) in diethyl ether a rapid intramolecular 1,4 proton shift takes place with the formation of 1-phenylbutyllithium (5).Similarly, although somewhat more slowly, 5-phenylpentyllithium (82) rearranges to 1-phenylpentyllithium (83) via 1,5 proton transfer.The corresponding rearrangements by 1,2 or 1,3 hydrogen shifts, however, starting with 2-phenylethyllithium (1) and 3-phenylpropyllithium (54), respectively, were not detected.With 3-phenylpropyllithium (54) a slow intramolecular 1,5 transfer an ortho proton is observed instead, yielding o-propylphenyllithium (100).The corresponding 1,6 shift with 4-phenylbutyllithium (2) was also detected in a minor amount in addition to the 1,4 proton shift already mentioned.There is no indication, however, for a 1,4 transfer of an ortho proton in 2-phenylethyllithium (1).The reaction products in this case can be exclusively explained by intermolecular transmetallation reactions.All ω-phenylalkyllithium compounds under investigation show interesting side and secondary reactions being rather different in deuterated solvents and in deuteriumfree solvents, respectively, due to the isotope effects.The analysis of the products is accomplished by 1H-NMR spectroscopy and, after derivatization, with the help of a GC-MS-combination.Stereoelectronic reasons are made responsible for the failure of the intramolecular 1,2 and 1,3 proton shift in these systems.
