Articles producció científica> Química Analítica i Química Orgànica

New Chiral P-N Ligands for the Regio- and Stereoselective Pd-Catalyzed Dimerization of Styrene

  • Identification data

    Identifier: imarina:6024479
    Authors:
    Fanfoni, LidiaMeduri, AngeloZangrando, EnnioCastillon, SergioFelluga, FulviaMilani, Barbara
    Abstract:
    Two new chiral, enantiomerically pure, hybrid P-N ligands, namely (2R,5S)-2-phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octan-4-one (1) and (2R,5S)-2phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octane (2), have been synthesized starting from L-proline. The two ligands differ in the presence or not of a carbonyl group in the diazaphosphane ring. Their coordination chemistry towards Pd(II) was studied by reacting them with [Pd(CH3)Cl(cod)]. A different behaviour was observed: ligand 2 shows the expected bidentate chelating behaviour leading to the mononuclear Pd-complex, while ligand 1 acts as a terdentate ligand giving a dinuclear species. The corresponding cationic derivatives were obtained from the palladium neutral complexes, both as mono-and dinuclear derivatives, and tested as precatalysts for styrene dimerization, yielding E-1,3-diphenyl-1-butene regio- and stereoselectively as the sole product. A detailed analysis of the catalytic behaviour is reported.
  • Others:

    Author, as appears in the article.: Fanfoni, Lidia; Meduri, Angelo; Zangrando, Ennio; Castillon, Sergio; Felluga, Fulvia; Milani, Barbara;
    Department: Química Analítica i Química Orgànica
    URV's Author/s: Castillón Miranda, Sergio
    Keywords: Rhodium(i) Quinolines Polymerization Pd(ii) complexes Palladium(ii) complexes Palladium Oligomerization Nickel(ii) complexes Hybrid phosphorus-nitrogen ligands Ethylene Co/ethylene Alternating copolymerization Alkene dimerization
    Abstract: Two new chiral, enantiomerically pure, hybrid P-N ligands, namely (2R,5S)-2-phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octan-4-one (1) and (2R,5S)-2phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octane (2), have been synthesized starting from L-proline. The two ligands differ in the presence or not of a carbonyl group in the diazaphosphane ring. Their coordination chemistry towards Pd(II) was studied by reacting them with [Pd(CH3)Cl(cod)]. A different behaviour was observed: ligand 2 shows the expected bidentate chelating behaviour leading to the mononuclear Pd-complex, while ligand 1 acts as a terdentate ligand giving a dinuclear species. The corresponding cationic derivatives were obtained from the palladium neutral complexes, both as mono-and dinuclear derivatives, and tested as precatalysts for styrene dimerization, yielding E-1,3-diphenyl-1-butene regio- and stereoselectively as the sole product. A detailed analysis of the catalytic behaviour is reported.
    Thematic Areas: Zootecnia / recursos pesqueiros Saúde coletiva Química Psicología Planejamento urbano e regional / demografia Physical and theoretical chemistry Pharmaceutical science Organic chemistry Odontología Nutrição Molecular medicine Medicine (miscellaneous) Medicina veterinaria Medicina iii Medicina ii Medicina i Materiais Matemática / probabilidade e estatística Interdisciplinar Geografía General medicine Farmacia Ensino Engenharias iv Engenharias iii Engenharias ii Engenharias i Educação física Economia Drug discovery Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências ambientais Ciências agrárias i Ciência de alimentos Ciência da computação Chemistry, organic Chemistry, multidisciplinary Chemistry (miscellaneous) Biotecnología Biodiversidade Biochemistry & molecular biology Astronomia / física Analytical chemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1420-3049
    Author's mail: sergio.castillon@urv.cat
    Author identifier: 0000-0002-0690-7549
    Record's date: 2023-02-18
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://www.mdpi.com/1420-3049/16/2/1804
    Papper original source: Molecules. 16 (2): 1804-1824
    APA: Fanfoni, Lidia; Meduri, Angelo; Zangrando, Ennio; Castillon, Sergio; Felluga, Fulvia; Milani, Barbara; (2011). New Chiral P-N Ligands for the Regio- and Stereoselective Pd-Catalyzed Dimerization of Styrene. Molecules, 16(2), 1804-1824. DOI: 10.3390/molecules16021804
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.3390/molecules16021804
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2011
    Publication Type: Journal Publications
  • Keywords:

    Analytical Chemistry,Biochemistry & Molecular Biology,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Chemistry, Organic,Drug Discovery,Medicine (Miscellaneous),Molecular Medicine,Organic Chemistry,Pharmaceutical Science,Physical and Theoretical Chemistry
    Rhodium(i)
    Quinolines
    Polymerization
    Pd(ii) complexes
    Palladium(ii) complexes
    Palladium
    Oligomerization
    Nickel(ii) complexes
    Hybrid phosphorus-nitrogen ligands
    Ethylene
    Co/ethylene
    Alternating copolymerization
    Alkene dimerization
    Zootecnia / recursos pesqueiros
    Saúde coletiva
    Química
    Psicología
    Planejamento urbano e regional / demografia
    Physical and theoretical chemistry
    Pharmaceutical science
    Organic chemistry
    Odontología
    Nutrição
    Molecular medicine
    Medicine (miscellaneous)
    Medicina veterinaria
    Medicina iii
    Medicina ii
    Medicina i
    Materiais
    Matemática / probabilidade e estatística
    Interdisciplinar
    Geografía
    General medicine
    Farmacia
    Ensino
    Engenharias iv
    Engenharias iii
    Engenharias ii
    Engenharias i
    Educação física
    Economia
    Drug discovery
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências ambientais
    Ciências agrárias i
    Ciência de alimentos
    Ciência da computação
    Chemistry, organic
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Biotecnología
    Biodiversidade
    Biochemistry & molecular biology
    Astronomia / física
    Analytical chemistry
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