Articles producció científica> Química Física i Inorgànica

Indene Derived Phosphorus-Thioether Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

  • Identification data

    Identifier: imarina:9187118
    Authors:
    Margalef, JessicaBiosca, Mariade la Cruz-Sanchez, PolCaldentey, XiscoRodriguez-Escrich, CarlesPamies, OscarPericas, Miquel A.Dieguez, Montserrat
    Abstract:
    A family of phosphite/phosphinite-thioether ligands have been tested in the Ir-catalyzed asymmetric hydrogenation of a range of olefins (50 substrates in total). The presented ligands are synthesized in three steps from cheap indene and they are air-stable solids. Their modular architecture has been crucial to maximize the catalytic performance for each type of substrate. Improving most Ir-catalysts reported so far, this ligand family presents a broader substrate scope, covering different substitution patterns with different functional groups, ranging from unfunctionalized olefins, through olefins with poorly coordinative groups, to olefins with coordinative functional groups. alpha,beta-Unsaturated acyclic and cyclic esters, ketones and amides werehydrogenated in enantioselectivities ranging from 83 to 99% ee. Enantioselectivities ranging from 91 to 98% ee were also achieved for challenging substrates such as unfunctionalized 1,1 '-disubstituted olefins, functionalized tri- and 1,1 '-disubstituted vinyl phosphonates, and beta-cyclic enamides. The catalytic performance of the Ir-ligand assemblies was maintained when the environmentally benign 1,2-propylene carbonate was used as solvent.
  • Others:

    Author, as appears in the article.: Margalef, Jessica; Biosca, Maria; de la Cruz-Sanchez, Pol; Caldentey, Xisco; Rodriguez-Escrich, Carles; Pamies, Oscar; Pericas, Miquel A.; Dieguez, Montserrat;
    Department: Química Física i Inorgànica
    URV's Author/s: Biosca Brull, Maria / De La Cruz Sánchez Badia, Pol / Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar
    Keywords: Β-cyclic enamides Α-β unsaturated compounds Phosphorus-thioether ligands Iridium Beta-cyclic enamides Asymmetric hydrogenation Alpha-beta unsaturated compounds
    Abstract: A family of phosphite/phosphinite-thioether ligands have been tested in the Ir-catalyzed asymmetric hydrogenation of a range of olefins (50 substrates in total). The presented ligands are synthesized in three steps from cheap indene and they are air-stable solids. Their modular architecture has been crucial to maximize the catalytic performance for each type of substrate. Improving most Ir-catalysts reported so far, this ligand family presents a broader substrate scope, covering different substitution patterns with different functional groups, ranging from unfunctionalized olefins, through olefins with poorly coordinative groups, to olefins with coordinative functional groups. alpha,beta-Unsaturated acyclic and cyclic esters, ketones and amides werehydrogenated in enantioselectivities ranging from 83 to 99% ee. Enantioselectivities ranging from 91 to 98% ee were also achieved for challenging substrates such as unfunctionalized 1,1 '-disubstituted olefins, functionalized tri- and 1,1 '-disubstituted vinyl phosphonates, and beta-cyclic enamides. The catalytic performance of the Ir-ligand assemblies was maintained when the environmentally benign 1,2-propylene carbonate was used as solvent.
    Thematic Areas: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: maria.biosca@urv.cat pol.delacruzsanchez@estudiants.urv.cat pol.delacruzsanchez@estudiants.urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-9116-6318 0000-0002-2352-8508 0000-0002-8450-0656
    Record's date: 2024-07-27
    Papper version: info:eu-repo/semantics/submittedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202100069
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Advanced Synthesis & Catalysis. 363 (19): 4561-4574
    APA: Margalef, Jessica; Biosca, Maria; de la Cruz-Sanchez, Pol; Caldentey, Xisco; Rodriguez-Escrich, Carles; Pamies, Oscar; Pericas, Miquel A.; Dieguez, Mo (2021). Indene Derived Phosphorus-Thioether Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups. Advanced Synthesis & Catalysis, 363(19), 4561-4574. DOI: 10.1002/adsc.202100069
    Article's DOI: 10.1002/adsc.202100069
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2021
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Β-cyclic enamides
    Α-β unsaturated compounds
    Phosphorus-thioether ligands
    Iridium
    Beta-cyclic enamides
    Asymmetric hydrogenation
    Alpha-beta unsaturated compounds
    Química
    Organic chemistry
    Materiais
    Engenharias iv
    Engenharias ii
    Ciências biológicas ii
    Ciência de alimentos
    Chemistry, organic
    Chemistry, applied
    Catalysis
    Biodiversidade
    Astronomia / física
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