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Synthesis and reactivity of Pd(II) imidoyl complexes obtained by insertion of isocyanoferrocene into the Pd–C bonds of orthopalladated precursors

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10472800" target="_blank" >RIV/00216208:11310/23:10472800 - isvavai.cz</a>

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=3xRB2SMaqE" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=3xRB2SMaqE</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/d3dt02717a" target="_blank" >10.1039/d3dt02717a</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis and reactivity of Pd(II) imidoyl complexes obtained by insertion of isocyanoferrocene into the Pd–C bonds of orthopalladated precursors

  • Original language description

    While the multifaceted reactivity of organic isocyanides has been extensively demonstrated, that of their organometallic analogue, isocyanoferrocene (FcNC; Fc = ferrocenyl), has not yet been adequately explored. This contribution describes the syntheses of novel chelating Pd(II) imidoyl complexes, [(YCH2C6H4C(NFc)-κ(2)Y,C)PdCl(PR3)], by insertion of FcNC into the Pd-C bond of cyclopalladated precursors [(YCH2C6H4-κ(2)Y,C)PdCl(PR3)] (Y = Me2N, MeS, R = Ph, Me). The imidoyl complexes underwent facile alkylation with [Me3O][BF4] to produce the cationic aminocarbene complexes [{YCH2C6H4C(N(Me)Fc)-κ(2)Y,C}PdCl(PR3)][BF4]. All compounds were fully characterised using a combination of spectroscopic methods (NMR, FTIR and ESI MS), cyclic voltammetry and single-crystal X-ray crystallography. In addition, DFT calculations were used to describe the bonding in the two compound families. Analyses with intrinsic bond orbitals (IBOs) and the quantum theory of atoms in molecules (QTAIM) consistently pointed to the transformation of an X-type imidoyl C-ligand (sigma-organyl) into an L-type carbene donor upon alkylation, which has only a minor structural consequence. Also reported is the unexpected conversion of the imidoyl complex [(Me2NCH2C6H4C(NFc)-κ(2)N,C)PdCl(PPh3)] into (Z)-2,2-dimethyl-1-(ferrocenylimino)isoindolin-2-ium tetrafluoroborate as a reductive elimination product, which was induced by Lewis and Bronsted acids.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - 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

  • Project

  • Continuities

    S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2023

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Dalton Transactions

  • ISSN

    1477-9226

  • e-ISSN

    1477-9234

  • Volume of the periodical

    52

  • Issue of the periodical within the volume

    47

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    10

  • Pages from-to

    17701-17710

  • UT code for WoS article

    001085539700001

  • EID of the result in the Scopus database

    2-s2.0-85174530268