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  1. Article ; Online: Reactions promoted by hypervalent iodine reagents and boron Lewis acids.

    Dasgupta, Ayan / Thiehoff, Christian / Newman, Paul D / Wirth, Thomas / Melen, Rebecca L

    Organic & biomolecular chemistry

    2022  Volume 19, Issue 22, Page(s) 4852–4865

    Abstract: Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis. Due to similar reactivities, λ3-iodanes have presented themselves as viable alternatives for many transformations ... ...

    Abstract Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis. Due to similar reactivities, λ3-iodanes have presented themselves as viable alternatives for many transformations dominated by transition metals whilst mitigating some of the associated drawbacks of metal systems. As showcased by recent reports, boranes can adopt a dual role in hypervalent iodine chemistry that surpasses mere activation of the hypervalent iodine reagent. Increased efforts to harness this potential with diverse boranes will uncover exciting reactivity with high applicability across various disciplines including adoption in the pharmaceutical sciences. This review will be relevant to the wider synthetic community including organic, inorganic, materials, and medicinal chemists due to the versatility of hypervalent iodine chemistry especially in combination with borane activation or participation. We aim to highlight the development of hypervalent iodine compounds including their structure, bonding, synthesis and utility in metal-free organic synthesis in combination with Lewis acidic boranes.
    Language English
    Publishing date 2022-01-17
    Publishing country England
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d1ob00740h
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis.

    Sarie, Jérôme C / Thiehoff, Christian / Neufeld, Jessica / Daniliuc, Constantin G / Gilmour, Ryan

    Angewandte Chemie (International ed. in English)

    2020  Volume 59, Issue 35, Page(s) 15069–15075

    Abstract: The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I) ...

    Abstract The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF
    Language English
    Publishing date 2020-06-09
    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.202005181
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres.

    Scheidt, Felix / Neufeld, Jessica / Schäfer, Michael / Thiehoff, Christian / Gilmour, Ryan

    Organic letters

    2018  Volume 20, Issue 24, Page(s) 8073–8076

    Abstract: A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, ... ...

    Abstract A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF
    Language English
    Publishing date 2018-12-11
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.8b03794
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Validating the 1,2-Difluoro Motif As a Hybrid Bioisostere of CF

    Erdeljac, Nathalie / Thiehoff, Christian / Jumde, Ravindra P / Daniliuc, Constantin G / Höppner, Sandra / Faust, Andreas / Hirsch, Anna K H / Gilmour, Ryan

    Journal of medicinal chemistry

    2020  Volume 63, Issue 11, Page(s) 6225–6237

    Abstract: Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by ... ...

    Abstract Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by advances in structural biology. Herein, we harness MMPs 2, 8, 9, and 13 to validate the
    MeSH term(s) Barbiturates/chemistry ; Barbiturates/metabolism ; Binding Sites ; Catalytic Domain ; Crystallography, X-Ray ; Fluorine/chemistry ; Isoenzymes/antagonists & inhibitors ; Isoenzymes/metabolism ; Matrix Metalloproteinase Inhibitors/chemistry ; Matrix Metalloproteinase Inhibitors/metabolism ; Matrix Metalloproteinases/chemistry ; Matrix Metalloproteinases/metabolism ; Molecular Conformation ; Molecular Docking Simulation ; Structure-Activity Relationship
    Chemical Substances Barbiturates ; Isoenzymes ; Matrix Metalloproteinase Inhibitors ; Fluorine (284SYP0193) ; Matrix Metalloproteinases (EC 3.4.24.-)
    Language English
    Publishing date 2020-05-22
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.0c00648
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Deconstructing the Catalytic, Vicinal Difluorination of Alkenes: HF-Free Synthesis and Structural Study of p-TolIF

    Sarie, Jérôme C / Thiehoff, Christian / Mudd, Richard J / Daniliuc, Constantin G / Kehr, Gerald / Gilmour, Ryan

    The Journal of organic chemistry

    2017  Volume 82, Issue 22, Page(s) 11792–11798

    Abstract: Recently, contemporaneous strategies to achieve the vicinal difluorination of alkenes via an I(I)/I(III) catalysis manifold were independently reported by this laboratory and by Jacobsen and co-workers. Both strategies proceed through a transient ArI(III) ...

    Abstract Recently, contemporaneous strategies to achieve the vicinal difluorination of alkenes via an I(I)/I(III) catalysis manifold were independently reported by this laboratory and by Jacobsen and co-workers. Both strategies proceed through a transient ArI(III)F
    Language English
    Publishing date 2017-11-17
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b01671
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines.

    Scheidt, Felix / Thiehoff, Christian / Yilmaz, Gülay / Meyer, Stephanie / Daniliuc, Constantin G / Kehr, Gerald / Gilmour, Ryan

    Beilstein journal of organic chemistry

    2018  Volume 14, Page(s) 1021–1027

    Abstract: Herein, we describe a catalytic fluorooxygenation of readily ... ...

    Abstract Herein, we describe a catalytic fluorooxygenation of readily accessible
    Language English
    Publishing date 2018-05-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.14.88
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Deconstructing the Catalytic, Vicinal Difluorination of Alkenes: HF-Free Synthesis and Structural Study of p-TolIF2

    Sarie, Jérôme C / Daniliuc Constantin G / Gilmour Ryan / Kehr Gerald / Mudd Richard J / Thiehoff Christian

    Journal of organic chemistry. 2017 Nov. 17, v. 82, no. 22

    2017  

    Abstract: Recently, contemporaneous strategies to achieve the vicinal difluorination of alkenes via an I(I)/I(III) catalysis manifold were independently reported by this laboratory and by Jacobsen and co-workers. Both strategies proceed through a transient ArI(III) ...

    Abstract Recently, contemporaneous strategies to achieve the vicinal difluorination of alkenes via an I(I)/I(III) catalysis manifold were independently reported by this laboratory and by Jacobsen and co-workers. Both strategies proceed through a transient ArI(III)F₂ species generated by oxidation of the ArI catalyst. Herein, an efficient synthesis of p-TolIF₂ from p-TolI and Selectfluor is presented, together with a crystallographic and spectroscopic study. To mitigate safety concerns and simplify reaction execution, an HF-free protocol was devised employing CsF as a substitute fluoride source. The study provides insight into the initial I(I)→I(III) oxidation stage of the catalytic protocol using Selectfluor.
    Keywords alkenes ; catalysts ; catalytic activity ; chemical structure ; fluorides ; organic chemistry ; oxidation ; spectral analysis
    Language English
    Dates of publication 2017-1117
    Size p. 11792-11798.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Facs.joc.7b01671
    Database NAL-Catalogue (AGRICOLA)

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