50704-52-4Relevant academic research and scientific papers
Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).
Aldehyde as a Traceless Directing Group for Regioselective C-H Alkylation Catalyzed by Rhodium(III) in Air
Chen, Si-Qi,Fan, Juan,Li, Chao-Jun,Li, Xin-Ran,Liu, Zhong-Wen,Shi, Xian-Ying
supporting information, p. 1259 - 1264 (2020/03/13)
The aromatic aldehyde as a traceless directing group for the regionselective C-H alkylation catalyzed by rhodium(III) under aerobic atmospheric conditions has been developed. The process involves an aldehyde assisted direct addition of C-H bond to unsaturated electrophiles of acrylates or acrylic acids, and the subsequent decarbonylation. A trace amount of water is found to favor the reaction.
Palladium-Catalyzed Alkoxycarbonylation of sec-Benzylic Ethers
Beller, Matthias,Jackstell, Ralf,Maes, Bert U. W.,Schneider, Carolin
supporting information, (2020/02/25)
Herein, we report the palladium-catalyzed synthesis of 3-arylpropionate esters starting from secondary benzylic ethers. With this investigation it could be shown that ethers are suitable starting materials in addition to the established carbonylation reactions of olefins, alcohols, or aryl halides.
Meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity
Liu, Luo-Yan,Qiao, Jennifer X.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan
supporting information, p. 14870 - 14877 (2019/10/02)
Controlling site selectivity of C-H activation without using a directing group remains a significant challenge. While Pd(II) catalysts modulated by a mutually repulsive pyridine-type ligand have been shown to favor the relatively electron-rich carbon centers of arenes, reversing the selectivity to favor palladation at the relatively electron-deficient positions has not been possible. Herein we report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chromane with exclusive meta site selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO2Me), as well as taking advantage of the statistics, are essential for achieving the exclusive meta selectivity.
Synthesis method of dihydrocinnamate type compound
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Paragraph 0014-017; 0022-0025, (2019/03/30)
The invention discloses a synthesis method of a dihydrocinnamate type compound. The method takes a dichloro(pentamethylcyclopentadienyl)rhodium dimer as a catalyst and a formyl o-C-H bond of aromaticaldehyde and alpha,beta-unsaturated ester type compound
Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis
Unelius, C. Rikard,Bohman, Bj?rn,Nordlander, G?ran
, p. 11797 - 11805 (2018/11/21)
This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.
NRF2 REGULATORS
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Page/Page column 186, (2017/01/02)
Provided are aryl analogs,pharmaceutical compositions containing them and their use as NRF2 regulators.
A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: Indirect use of carbon dioxide
Gehrtz,Hirschbeck,Fleischer
supporting information, p. 12574 - 12577 (2015/08/06)
Herein, we report a Pd-catalysed alkoxycarbonylation of alkenes based on the use of a recyclable CO2 reduction product, the crystalline and air-stable N-formylsaccharin, as a CO surrogate. The carbonylation proceeds under ambient conditions in an exceptionally complementary regioselective fashion yielding the desired branched products from styrene derivatives and valuable linear esters from alkyl-substituted alkenes.
Xylochemistry - Making Natural Products Entirely from Wood
Stubba, Daniel,Lahm, Günther,Geffe, Mario,Runyon, Jason W.,Arduengo, Anthony J.,Opatz, Till
, p. 14187 - 14189 (2016/01/25)
The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood-derived building blocks (xylochemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches.
RE12 derivatives displaying Vaccinia H1-related phosphatase (VHR) inhibition in the presence of detergent and their anti-proliferative activity against HeLa cells
Thuaud, Frederic,Kojima, Shuntaro,Hirai, Go,Oonuma, Kana,Tsuchiya, Ayako,Uchida, Takako,Tsuchimoto, Teruhisa,Sodeoka, Mikiko
, p. 2771 - 2782 (2014/05/06)
New derivatives of Vaccinia H1-related phosphatase (VHR) inhibitor RE12 (5) were designed by replacing the long straight alkyl chain with other hydrophobic functionalities containing two aromatic rings, with the aim of obtaining potent, cell-active inhibitors. We established a direct coupling reaction between tetronic acid derivative and thioimidate to prepare the RE derivatives 6a-6i efficiently. These compounds all showed VHR-inhibitory activity in the presence of 0.001% NP-40, whereas RE12 (5) was inactive under this condition, even at 100 μM. Further structure-activity studies focused on terminal substitution afforded trifluoromethyl derivative 6k (RE176) and nitro derivative 6l (RE177). The IC50 value of 6l in the presence of NP-40 was almost equivalent to that of RE12 (5) in its absence. Compound 6k (RE176) potently inhibited proliferation of HeLa cells.
