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  1. Article ; Online: Mild Divergent Semireductive Transformations of Secondary and Tertiary Amides via Zirconocene Hydride Catalysis.

    Kehner, Rebecca A / Zhang, Ge / Bayeh-Romero, Liela

    Journal of the American Chemical Society

    2023  Volume 145, Issue 9, Page(s) 4921–4927

    Abstract: The mild catalytic partial reduction of amides to imines has proven to be a challenging synthetic transformation, with many transition metals directly reducing these substrates to amines. Herein, we report a mild, catalytic method for the semireduction ... ...

    Abstract The mild catalytic partial reduction of amides to imines has proven to be a challenging synthetic transformation, with many transition metals directly reducing these substrates to amines. Herein, we report a mild, catalytic method for the semireduction of both secondary and tertiary amides via zirconocene hydride catalysis. Utilizing just 5 mol % of Cp
    Language English
    Publishing date 2023-02-21
    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.2c11786
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Expanding Zirconocene Hydride Catalysis:

    Kehner, Rebecca A / Hewitt, Matthew Christian / Bayeh-Romero, Liela

    ACS catalysis

    2022  Volume 12, Issue 3, Page(s) 1758–1763

    Abstract: Despite the wide use and popularity of metal hydride catalysis, methods utilizing zirconium hydride catalysts remain underexplored. Here, we report the development of a mild method for ... ...

    Abstract Despite the wide use and popularity of metal hydride catalysis, methods utilizing zirconium hydride catalysts remain underexplored. Here, we report the development of a mild method for the
    Language English
    Publishing date 2022-01-18
    Publishing country United States
    Document type Journal Article
    ISSN 2155-5435
    ISSN 2155-5435
    DOI 10.1021/acscatal.2c00079
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release.

    Lubaev, Alexandra E / Rathnayake, Manjula D / Eze, Favour / Bayeh-Romero, Liela

    Journal of the American Chemical Society

    2022  Volume 144, Issue 29, Page(s) 13294–13301

    Abstract: A new strategy is described for the Lewis base-catalyzed bromochlorination of unsaturated systems that is mechanistically distinct from prior methodologies. The novelty of this method hinges on the utilization of thionyl chloride as a latent chloride ... ...

    Abstract A new strategy is described for the Lewis base-catalyzed bromochlorination of unsaturated systems that is mechanistically distinct from prior methodologies. The novelty of this method hinges on the utilization of thionyl chloride as a latent chloride source in combination with as little as 1 mol % of triphenylphosphine or triphenylphosphine oxide as Lewis basic activators. This metal-free, catalytic chemo-, regio-, and diastereoselective bromochlorination of alkenes and alkynes exhibits excellent site selectivity in polyunsaturated systems and provides access to a wide variety of vicinal bromochlorides with up to >20:1 regio- and diastereoselectivity. The precision installation of Br, Cl, and I in various combinations is also demonstrated by simply varying the commercial halogenating reagents employed. Notably, when a chiral Lewis base promoter is employed, an enantioselective bromochlorination of chalcones is possible with up to a 92:8 enantiomeric ratio when utilizing only 1-3 mol % of (DHQD)
    MeSH term(s) Alkenes ; Catalysis ; Chlorides ; Halogens ; Lewis Bases ; Stereoisomerism
    Chemical Substances Alkenes ; Chlorides ; Halogens ; Lewis Bases
    Language English
    Publishing date 2022-07-12
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.2c04588
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release

    Lubaev, Alexandra E. / Rathnayake, Manjula D. / Eze, Favour / Bayeh-Romero, Liela

    Journal of the American Chemical Society. 2022 July 12, v. 144, no. 29

    2022  

    Abstract: A new strategy is described for the Lewis base-catalyzed bromochlorination of unsaturated systems that is mechanistically distinct from prior methodologies. The novelty of this method hinges on the utilization of thionyl chloride as a latent chloride ... ...

    Abstract A new strategy is described for the Lewis base-catalyzed bromochlorination of unsaturated systems that is mechanistically distinct from prior methodologies. The novelty of this method hinges on the utilization of thionyl chloride as a latent chloride source in combination with as little as 1 mol % of triphenylphosphine or triphenylphosphine oxide as Lewis basic activators. This metal-free, catalytic chemo-, regio-, and diastereoselective bromochlorination of alkenes and alkynes exhibits excellent site selectivity in polyunsaturated systems and provides access to a wide variety of vicinal bromochlorides with up to >20:1 regio- and diastereoselectivity. The precision installation of Br, Cl, and I in various combinations is also demonstrated by simply varying the commercial halogenating reagents employed. Notably, when a chiral Lewis base promoter is employed, an enantioselective bromochlorination of chalcones is possible with up to a 92:8 enantiomeric ratio when utilizing only 1–3 mol % of (DHQD)₂PHAL.
    Keywords Lewis bases ; alkenes ; alkynes ; chalcones ; chlorides ; diastereoselectivity ; enantioselectivity
    Language English
    Dates of publication 2022-0712
    Size p. 13294-13301.
    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.2c04588
    Database NAL-Catalogue (AGRICOLA)

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  5. Article ; Online: Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.

    Bayeh-Romero, Liela / Buchwald, Stephen L

    Journal of the American Chemical Society

    2019  Volume 141, Issue 35, Page(s) 13788–13794

    Abstract: The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed ... ...

    Abstract The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
    MeSH term(s) Alkadienes/chemical synthesis ; Alkadienes/chemistry ; Alkynes/chemistry ; Catalysis ; Copper/chemistry ; Molecular Structure ; Pyrroles/chemical synthesis ; Pyrroles/chemistry
    Chemical Substances Alkadienes ; Alkynes ; Pyrroles ; Copper (789U1901C5)
    Language English
    Publishing date 2019-08-21
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.9b07582
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes

    Bayeh-Romero, Liela / Buchwald, Stephen L

    Journal of the American Chemical Society. 2019 Aug. 17, v. 141, no. 35

    2019  

    Abstract: The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed ... ...

    Abstract The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
    Keywords catalytic activity ; chemoselectivity ; enantioselective synthesis ; hydrides ; moieties
    Language English
    Dates of publication 2019-0817
    Size p. 13788-13794.
    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.9b07582
    Database NAL-Catalogue (AGRICOLA)

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    Kategorien

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