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  1. Article ; Online: Synthesis of 1,1-Diboryl Alkenes Using the Boryl-Heck Reaction.

    Idowu, Olamide O / Hayes, Jacob C / Reid, William B / Watson, Donald A

    Organic letters

    2021  Volume 23, Issue 12, Page(s) 4838–4842

    Abstract: The synthesis of 1,1-diboryl alkenes from terminal alkenes is reported. 1,1-Regioselective addition is observed for both conjugated and unconjugated alkenes, allowing for a single method to prepare a wide range of 1,1-diboryl alkenes. ...

    Abstract The synthesis of 1,1-diboryl alkenes from terminal alkenes is reported. 1,1-Regioselective addition is observed for both conjugated and unconjugated alkenes, allowing for a single method to prepare a wide range of 1,1-diboryl alkenes.
    MeSH term(s) Alkenes/chemical synthesis ; Alkenes/chemistry ; Molecular Structure ; Stereoisomerism
    Chemical Substances Alkenes
    Language English
    Publishing date 2021-05-27
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.1c01567
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Reactions of Benzylboronate Nucleophiles.

    Barker, Timothy J / Bogatkevich, Andrew / Crowder, Dallas W / Gierszal, Sophia G / Hayes, Jacob C / Hollerbach, Michael R / Russell, Richard W

    Synthesis

    2023  Volume 55, Issue 17, Page(s) 2639–2647

    Abstract: This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This ... ...

    Abstract This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines.
    Language English
    Publishing date 2023-05-08
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-2072-2754
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Benzylation of Imines with Activated Boronate Nucleophiles.

    Hollerbach, Michael R / Hayes, Jacob C / Barker, Timothy J

    European journal of organic chemistry

    2019  Volume 2019, Issue 7, Page(s) 1646–1648

    Abstract: Benzylation reactions ... ...

    Abstract Benzylation reactions of
    Language English
    Publishing date 2019-01-21
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1475010-7
    ISSN 1099-0690 ; 1434-193X
    ISSN (online) 1099-0690
    ISSN 1434-193X
    DOI 10.1002/ejoc.201801804
    Database MEDical Literature Analysis and Retrieval System OnLINE

    Full text online

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  4. Article: Nucleophilic Addition of Benzylboronates to Activated Ketones.

    Hayes, Jacob C / Hollerbach, Michael R / Barker, Timothy J

    Tetrahedron letters

    2019  Volume 61, Issue 7

    Abstract: A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In ... ...

    Abstract A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF
    Language English
    Publishing date 2019-12-16
    Publishing country England
    Document type Journal Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2019.151505
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  5. Article: Selected Ion Monitoring Using Low-Cost Mass Spectrum Detectors Provides a Rapid, General, and Accurate Method for Enantiomeric Excess Determination in High-Throughput Experimentation.

    Korch, Katerina M / Hayes, Jacob C / Kim, Raphael S / Sampson, Jessica / Kelly, Austin T / Watson, Donald A

    ACS catalysis

    2022  Volume 12, Issue 11, Page(s) 6737–6745

    Abstract: High-Throughput Experimentation (HTE) workflows are efficient means of surveying a broad array of chiral catalysts in the development of catalytic asymmetric reactions. However, use of traditional HPLC-UV/vis methodology to determine enantiomeric excess ( ...

    Abstract High-Throughput Experimentation (HTE) workflows are efficient means of surveying a broad array of chiral catalysts in the development of catalytic asymmetric reactions. However, use of traditional HPLC-UV/vis methodology to determine enantiomeric excess (ee) from the resulting reactions is often hampered by co-elution of other reaction components, resulting in erroneous ee determination when crude samples are used, and ultimately requiring product isolation prior to ee analysis. In this study, using four published reactions selected as model systems, we demonstrate that the use of LC-MS, SFC-MS, and selected ion monitoring (SIM) mass chromatography provides a highly accurate means to determine ee of products in crude reaction samples using commonplace, low-cost MS detectors. By using ion selection, co-eluting signals can be deconvoluted to provide accurate integrations of the target analytes. We also show that this method is effective for samples lacking UV/vis chromophores, making it ideal for HTE workflows in asymmetric catalysis.
    Language English
    Publishing date 2022-05-23
    Publishing country United States
    Document type Journal Article
    ISSN 2155-5435
    ISSN 2155-5435
    DOI 10.1021/acscatal.2c01628
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Nucleophilic addition of benzylboronates to activated ketones

    Hayes, Jacob C / Hollerbach, Michael R / Barker, Timothy J

    Tetrahedron letters. 2020 Feb. 13, v. 61, no. 7

    2020  

    Abstract: A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In ... ...

    Abstract A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF2H ketone > CF3 ketone > aldehyde under these reaction conditions.
    Keywords Lewis acids ; Lewis bases ; aldehydes ; boronic acids ; chemical reactions ; chemoselectivity ; ketones ; moieties
    Language English
    Dates of publication 2020-0213
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2019.151505
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

    Order via subito

    This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

  7. Article: Reactions of Benzylboronate Nucleophiles

    Barker, Timothy J. / Bogatkevich, Andrew / Crowder, Dallas W. / Gierszal, Sophia G. / Hayes, Jacob C. / Hollerbach, Michael R. / Russell, Richard W.

    Synthesis

    2023  Volume 55, Issue 17, Page(s) 2639–2647

    Abstract: This short review summarizes our laboratory’s development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This ... ...

    Abstract This short review summarizes our laboratory’s development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones, and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines. 1

    Introduction 2

    1,2-Additions 3

    Additions to sp 3 Electrophiles 4

    Conclusion and Outlook
    Keywords boron ; benzylation ; Lewis base ; copper ; boronate
    Language English
    Publishing date 2023-04-12
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-2072-2754
    Database Thieme publisher's database

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