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Probing the Influence of Phosphine Substituents on the Donor and Catalytic Properties of Phosphinoferrocene Carboxamides: A Combined Experimental and Theoretical Study

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F17%3A10360167" target="_blank" >RIV/00216208:11310/17:10360167 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1021/acs.organomet.7b00181" target="_blank" >http://dx.doi.org/10.1021/acs.organomet.7b00181</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.organomet.7b00181" target="_blank" >10.1021/acs.organomet.7b00181</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Probing the Influence of Phosphine Substituents on the Donor and Catalytic Properties of Phosphinoferrocene Carboxamides: A Combined Experimental and Theoretical Study

  • Original language description

    The stereoelectronic influence of phosphine substituents on the coordination and catalytic properties of phosphinoferrocene carbox-amides was studied for the model compounds R2PfcCONHMe (1a-d), where fc = ferrocene-1,1&apos;-diyl and R = i-Pr (a), t-Bu (b), cyclohexyl (Cy; c), Ph (d), using experimental and DFT-computed parameters. The electronic parameters were examined via 1J(Se,P) coupling constants determined for R2P(Se)fcCONHMe (6a-d) and CO stretching frequencies of the Rh(I) complexes trans-[RhCl(CO)(1-kappa P)2] (7a-d); the steric properties of 1a-d were assessed through Tolman&apos;s ligand cone angles (theta) and solid angles (Omega). Generally, a very good agreement between the calculated and experimental values was observed. Whereas the donor ability of the amidophosphines was found to increase from 1d through 1a,c to 1b, the trends in steric demand suggested by the two parameters differed, reflecting the different spatial properties of the phosphine substituents. In situ NMR studies and catalytic tests on the Suzuki-Miyaura cross-coupling of 4-bromoanisole with a bicyclic 4-tolylborate to give 4-methyl-4&apos;-methoxybiphenyl using [Pd(eta(2):eta(2)-cod)(eta(2)-ma)] (cod = cycloocta-1,5-diene, ma = maleic anhydride) as a Pd(0) precursor revealed that different Pd-1 species (precatalysts) were formed from different ligands and participated in the reaction. Specifically, the bulky and electron-rich donor 1b favored the formation of [Pd(1b)(ma)], while the remaining ligands provided the corresponding bis-phosphine complexes [Pd(1)2(ma)]. The best results in terms of catalyst longevity and efficacy were observed for ligands 1a,c.

  • 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

    <a href="/en/project/7F14392" target="_blank" >7F14392: Phosphine Ligands for Environmentally Friendly C-C Bond Forming Reactions</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

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

    9

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    14

  • Pages from-to

    1828-1841

  • UT code for WoS article

    000401044300022

  • EID of the result in the Scopus database

    2-s2.0-85019047731