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Preferential cross-coupling of naphthol derivatives mediated by copper(II)

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F13%3A10192748" target="_blank" >RIV/00216208:11310/13:10192748 - isvavai.cz</a>

  • Alternative codes found

    RIV/61388963:_____/13:00399814

  • Result on the web

    <a href="http://dx.doi.org/10.1002/poc.3086" target="_blank" >http://dx.doi.org/10.1002/poc.3086</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/poc.3086" target="_blank" >10.1002/poc.3086</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Preferential cross-coupling of naphthol derivatives mediated by copper(II)

  • Original language description

    Preferential cross-coupling of differently N-substituted amides of 3-hydroxy-2-naphthoic acids 1 and 2 catalyzed by Cu(OH)Cl center dot TMEDA was observed. The reaction mechanism was investigated using mass spectrometry tools. It was shown that the complexation properties of the N-substituent significantly influence the properties of the corresponding copper complexes of the deprotonated compounds ([(1-H)Cu(TMEDA)](+) and [(2-H)Cu(TMEDA)](+)). Analysis of the fragmentation patterns of the copper complexes revealed that while the former is prone to the one electron oxidation of (1-H)(-), the latter has a larger binding energy between (2-H)(-) and copper(II). Interplay between the abundance of the copper complexes and their reactivities explains the preferential cross-coupling. The results are further supported by exploratory density functional theory calculations.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/GAP207%2F11%2F0338" target="_blank" >GAP207/11/0338: Reaction mechanisms in organometallic chemistry</a><br>

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)

Others

  • Publication year

    2013

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Journal of Physical Organic Chemistry

  • ISSN

    0894-3230

  • e-ISSN

  • Volume of the periodical

    26

  • Issue of the periodical within the volume

    9

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    9

  • Pages from-to

    715-723

  • UT code for WoS article

    000325920900006

  • EID of the result in the Scopus database