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  1. Article ; Online: Mechanistic Study of Arylsilane Oxidation through

    Rayment, Elizabeth J / Mekareeya, Aroonroj / Summerhill, Nick / Anderson, Edward A

    Journal of the American Chemical Society

    2017  Volume 139, Issue 17, Page(s) 6138–6145

    Abstract: The mechanism of the oxidation of arylsilanes to phenols has been investigated ... ...

    Abstract The mechanism of the oxidation of arylsilanes to phenols has been investigated using
    Language English
    Publishing date 2017-05-03
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.7b00357
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Mechanistic Study of Arylsilane Oxidation through 19F NMR Spectroscopy

    Rayment, Elizabeth J / Anderson Edward A / Mekareeya Aroonroj / Summerhill Nick

    Journal of the American Chemical Society. 2017 May 03, v. 139, no. 17

    2017  

    Abstract: The mechanism of the oxidation of arylsilanes to phenols has been investigated using ¹⁹F NMR spectroscopy. The formation of silanols in these reactions results from a rapid background equilibrium between silanol and alkoxysilane; the relative rates of ...

    Abstract The mechanism of the oxidation of arylsilanes to phenols has been investigated using ¹⁹F NMR spectroscopy. The formation of silanols in these reactions results from a rapid background equilibrium between silanol and alkoxysilane; the relative rates of reaction of these species was evaluated by modeling of concentration profiles obtained through ¹⁹F NMR spectroscopic reaction monitoring. Combining these results with a study of initial rates of phenol formation, and of substituent electronic effects, a mechanistic picture involving rapid and reversible formation of a pentavalent peroxide ate complex, prior to rate-limiting aryl migration, has evolved.
    Keywords nuclear magnetic resonance spectroscopy ; oxidation ; phenols
    Language English
    Dates of publication 2017-0503
    Size p. 6138-6145.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021%2Fjacs.7b00357
    Database NAL-Catalogue (AGRICOLA)

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  3. Article ; Online: Hydrogen-Bond-Enabled Dynamic Kinetic Resolution of Axially Chiral Amides Mediated by a Chiral Counterion.

    Fugard, Alison J / Lahdenperä, Antti S K / Tan, Jaqueline S J / Mekareeya, Aroonroj / Paton, Robert S / Smith, Martin D

    Angewandte Chemie (International ed. in English)

    2019  Volume 58, Issue 9, Page(s) 2795–2798

    Abstract: Non-biaryl atropisomers are valuable in medicine, materials, and catalysis, but their enantioselective synthesis remains a challenge. Herein, a counterion-mediated O-alkylation method for the generation of atropisomeric amides with an er up to 99:1 is ... ...

    Abstract Non-biaryl atropisomers are valuable in medicine, materials, and catalysis, but their enantioselective synthesis remains a challenge. Herein, a counterion-mediated O-alkylation method for the generation of atropisomeric amides with an er up to 99:1 is outlined. This dynamic kinetic resolution is enabled by the observation that the rate of racemization of atropisomeric naphthamides is significantly increased by the presence of an intramolecular O-H⋅⋅⋅NCO hydrogen bond. Upon O-alkylation of the H-bond donor, the barrier to rotation is significantly increased. Quantum calculations demonstrate that the intramolecular H-bond reduces the rotational barrier about the aryl-amide bond, stabilizing the planar transition state for racemization by approximately 40 kJ mol
    Language English
    Publishing date 2019-02-06
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201814362
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Mechanistic Insight into Palladium-Catalyzed Cycloisomerization: A Combined Experimental and Theoretical Study.

    Mekareeya, Aroonroj / Walker, P Ross / Couce-Rios, Almudena / Campbell, Craig D / Steven, Alan / Paton, Robert S / Anderson, Edward A

    Journal of the American Chemical Society

    2017  Volume 139, Issue 29, Page(s) 10104–10114

    Abstract: The cycloisomerization of enynes catalyzed by Pd(OAc) ...

    Abstract The cycloisomerization of enynes catalyzed by Pd(OAc)
    Language English
    Publishing date 2017-07-26
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.7b05436
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Copper-Catalyzed Synthesis and Applications of Yndiamides.

    Mansfield, Steven J / Christensen, Kirsten E / Thompson, Amber L / Ma, Kai / Jones, Michael W / Mekareeya, Aroonroj / Anderson, Edward A

    Angewandte Chemie (International ed. in English)

    2017  Volume 56, Issue 46, Page(s) 14428–14432

    Abstract: The first synthetic route to yndiamides, a novel class of double aza-substituted alkyne, has been established by the copper(I)-catalyzed cross-coupling of 1,1-dibromoenamides with nitrogen nucleophiles. The utility of these compounds is demonstrated in a ...

    Abstract The first synthetic route to yndiamides, a novel class of double aza-substituted alkyne, has been established by the copper(I)-catalyzed cross-coupling of 1,1-dibromoenamides with nitrogen nucleophiles. The utility of these compounds is demonstrated in a range of transition-metal-catalyzed and acid-catalyzed transformations to afford a wide variety of 1,2-diamide functionalized products.
    Language English
    Publishing date 2017-10-13
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201706915
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Mechanistic Insight into Palladium-Catalyzed Cycloisomerization: A Combined Experimental and Theoretical Study

    Mekareeya, Aroonroj / Alan Steven / Almudena Couce-Rios / Craig D. Campbell / Edward A. Anderson / P. Ross Walker / Robert S. Paton

    Journal of the American Chemical Society. 2017 July 26, v. 139, no. 29

    2017  

    Abstract: The cycloisomerization of enynes catalyzed by Pd(OAc)2 and bis-benzylidene ethylenediamine (bbeda) is a landmark methodology in transition-metal-catalyzed cycloisomerization. However, the mechanistic pathway by which this reaction proceeds has remained ... ...

    Abstract The cycloisomerization of enynes catalyzed by Pd(OAc)2 and bis-benzylidene ethylenediamine (bbeda) is a landmark methodology in transition-metal-catalyzed cycloisomerization. However, the mechanistic pathway by which this reaction proceeds has remained unclear for several decades. Here we describe mechanistic investigations into this reaction using enynamides, which deliver azacycles with high regio- and stereocontrol. Extensive 1H NMR spectroscopic studies and isotope effects support a palladium(II) hydride-mediated pathway and reveal crucial roles of bbeda, water, and the precise nature of the Pd(OAc)2 pre-catalyst. Computational studies support these mechanistic findings and lead to a clear picture of the origins of the high stereocontrol that can be achieved in this transformation, as well as suggesting a novel mechanism by which hydrometalation proceeds.
    Keywords catalytic activity ; isotopes ; nuclear magnetic resonance spectroscopy ; palladium ; spectral analysis
    Language English
    Dates of publication 2017-0726
    Size p. 10104-10114.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.7b05436
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  7. Article ; Online: Virtual screening for small-molecule pathway regulators by image-profile matching.

    Rohban, Mohammad H / Fuller, Ashley M / Tan, Ceryl / Goldstein, Jonathan T / Syangtan, Deepsing / Gutnick, Amos / DeVine, Ann / Nijsure, Madhura P / Rigby, Megan / Sacher, Joshua R / Corsello, Steven M / Peppler, Grace B / Bogaczynska, Marta / Boghossian, Andrew / Ciotti, Gabrielle E / Hands, Allison T / Mekareeya, Aroonroj / Doan, Minh / Gale, Jennifer P /
    Derynck, Rik / Turbyville, Thomas / Boerckel, Joel D / Singh, Shantanu / Kiessling, Laura L / Schwarz, Thomas L / Varelas, Xaralabos / Wagner, Florence F / Kafri, Ran / Eisinger-Mathason, T S Karin / Carpenter, Anne E

    Cell systems

    2022  Volume 13, Issue 9, Page(s) 724–736.e9

    Abstract: Identifying the chemical regulators of biological pathways is a time-consuming bottleneck in developing therapeutics and research compounds. Typically, thousands to millions of candidate small molecules are tested in target-based biochemical screens or ... ...

    Abstract Identifying the chemical regulators of biological pathways is a time-consuming bottleneck in developing therapeutics and research compounds. Typically, thousands to millions of candidate small molecules are tested in target-based biochemical screens or phenotypic cell-based screens, both expensive experiments customized to each disease. Here, our uncustomized, virtual, profile-based screening approach instead identifies compounds that match to pathways based on the phenotypic information in public cell image data, created using the Cell Painting assay. Our straightforward correlation-based computational strategy retrospectively uncovered the expected, known small-molecule regulators for 32% of positive-control gene queries. In prospective, discovery mode, we efficiently identified new compounds related to three query genes and validated them in subsequent gene-relevant assays, including compounds that phenocopy or pheno-oppose YAP1 overexpression and kill a Yap1-dependent sarcoma cell line. This image-profile-based approach could replace many customized labor- and resource-intensive screens and accelerate the discovery of biologically and therapeutically useful compounds.
    MeSH term(s) Cell Line ; Prospective Studies ; Retrospective Studies
    Language English
    Publishing date 2022-09-02
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 2854138-8
    ISSN 2405-4720 ; 2405-4712
    ISSN (online) 2405-4720
    ISSN 2405-4712
    DOI 10.1016/j.cels.2022.08.003
    Database MEDical Literature Analysis and Retrieval System OnLINE

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