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
—