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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61388963:_____/13:00399814

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F11%2F0338" target="_blank" >GAP207/11/0338: Reakční mechanismy v organometalické chemii</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

Journal of Physical Organic Chemistry

ISSN

0894-3230

e-ISSN

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Svazek periodika

26

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

715-723

Kód UT WoS článku

000325920900006

EID výsledku v databázi Scopus

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