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

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1002/poc.3086
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. 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. (en)
Title	Preferential cross-coupling of naphthol derivatives mediated by copper(II) Preferential cross-coupling of naphthol derivatives mediated by copper(II) (en)
skos:prefLabel	Preferential cross-coupling of naphthol derivatives mediated by copper(II) Preferential cross-coupling of naphthol derivatives mediated by copper(II) (en)
skos:notation	RIV/00216208:11310/13:10192748!RIV14-GA0-11310___
http://linked.open...avai/predkladatel	Přírodovědecká fakulta
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(GAP108/12/1356), P(GAP207/11/0338), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	9
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Roithová, Jana
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	98796
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/13:10192748
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	reaction mechanisms; mass spectrometry; DFT calculations; cross-coupling; copper; BINOL (en)
http://linked.open.../riv/klicoveSlovo	copper cross-coupling mass spectrometry reaction mechanisms DFT calculations BINOL
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[5CDC98A6ACA5]
http://linked.open...i/riv/nazevZdroje	Journal of Physical Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Reaction mechanisms in organometallic chemistry Polysilsesquioxane-based chiral hybrid organic-inorganic materials
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	26
http://linked.open...iv/tvurceVysledku	Hodačová, Jana Roithová, Jana Koščová, Simona
http://linked.open...ain/vavai/riv/wos	000325920900006
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	0894-3230
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/poc.3086
http://localhost/t...ganizacniJednotka	11310

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