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Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1'-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis

Result description

(Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2*H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1'-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(eta(5)-C5H4PMes2)(eta5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H- phosphonium/hydroborate product, [Fe(eta(5)-C5H4PHMes2){eta(5)-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich pi-systems (imine, enamine) as well as well as the electron-deficient carbon carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H-2 pressure, 50 degrees C).

Keywords

phosphineshydroborationfrustrated Lewis pairsferrocene

The result's identifiers

Alternative languages

  • Result language

    angličtina

  • Original language name

    Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1'-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis

  • Original language description

    (Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2*H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1'-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(eta(5)-C5H4PMes2)(eta5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H- phosphonium/hydroborate product, [Fe(eta(5)-C5H4PHMes2){eta(5)-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich pi-systems (imine, enamine) as well as well as the electron-deficient carbon carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H-2 pressure, 50 degrees C).

  • Czech name

  • Czech description

Classification

  • Type

    Jimp - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10402 - Inorganic and nuclear chemistry

Result continuities

Others

  • Publication year

    2017

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Organometallics

  • ISSN

    0276-7333

  • e-ISSN

  • Volume of the periodical

    36

  • Issue of the periodical within the volume

    15

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    7

  • Pages from-to

    2940-2946

  • UT code for WoS article

    000407869100028

  • EID of the result in the Scopus database

    2-s2.0-85027404745

Basic information

Result type

Jimp - Article in a specialist periodical, which is included in the Web of Science database

Jimp

OECD FORD

Inorganic and nuclear chemistry

Year of implementation

2017