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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F12%3A10128776%21RIV13-GA0-11310___
rdf:type
skos:Concept n8:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1002/anie.201204003
dcterms:description
The present %22gold-rush%22 in chemistry started in the nineties with a report of a gold-catalyzed addition of methanol to alkynes, which shook the conception of gold as an inert metal. Here, we present a mechanism of this reaction and demonstrate that actually two gold cations in cooperation activate the C-C triple bond and mediate the methanol addition, which results directly in formation of a diaurated intermediate. This reaction intermediate was detected by electrospray ionization mass spectrometry, labeling and infrared multiphoton dissociation spectroscopy, which clearly revealed the addition of the methoxy group to the C-C triple bond. The kinetics of the reaction was determined from NMR experiments. The experimental results are complemented by theoretical calculations, which provide an overall picture of the reaction mechanism. The present %22gold-rush%22 in chemistry started in the nineties with a report of a gold-catalyzed addition of methanol to alkynes, which shook the conception of gold as an inert metal. Here, we present a mechanism of this reaction and demonstrate that actually two gold cations in cooperation activate the C-C triple bond and mediate the methanol addition, which results directly in formation of a diaurated intermediate. This reaction intermediate was detected by electrospray ionization mass spectrometry, labeling and infrared multiphoton dissociation spectroscopy, which clearly revealed the addition of the methoxy group to the C-C triple bond. The kinetics of the reaction was determined from NMR experiments. The experimental results are complemented by theoretical calculations, which provide an overall picture of the reaction mechanism.
dcterms:title
Gold-Gold Cooperation in the Addition of Methanol to Alkynes Gold-Gold Cooperation in the Addition of Methanol to Alkynes
skos:prefLabel
Gold-Gold Cooperation in the Addition of Methanol to Alkynes Gold-Gold Cooperation in the Addition of Methanol to Alkynes
skos:notation
RIV/00216208:11310/12:10128776!RIV13-GA0-11310___
n8:predkladatel
n9:orjk%3A11310
n3:aktivita
n19:Z n19:P n19:I
n3:aktivity
I, P(GAP207/11/0338), Z(MSM0021620857)
n3:cisloPeriodika
33
n3:dodaniDat
n14:2013
n3:domaciTvurceVysledku
n7:2794489 n7:2213117 n7:7629338 n7:4889223 n7:8784477
n3:druhVysledku
n22:J
n3:duvernostUdaju
n16:S
n3:entitaPredkladatele
n20:predkladatel
n3:idSjednocenehoVysledku
138281
n3:idVysledku
RIV/00216208:11310/12:10128776
n3:jazykVysledku
n6:eng
n3:klicovaSlova
reaction intermediates; kinetics; ion spectroscopy; gold catalysis; density functional calculations
n3:klicoveSlovo
n4:kinetics n4:gold%20catalysis n4:reaction%20intermediates n4:density%20functional%20calculations n4:ion%20spectroscopy
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[B5E509F039E5]
n3:nazevZdroje
Angewandte Chemie - International Edition
n3:obor
n11:CC
n3:pocetDomacichTvurcuVysledku
5
n3:pocetTvurcuVysledku
5
n3:projekt
n10:GAP207%2F11%2F0338
n3:rokUplatneniVysledku
n14:2012
n3:svazekPeriodika
51
n3:tvurceVysledku
Roithová, Jana Jašíková, Lucie Váňa, Jiří Hybelbauerová, Simona Janková, Štěpánka
n3:wos
000307215900046
n3:zamer
n17:MSM0021620857
s:issn
1433-7851
s:numberOfPages
5
n15:doi
10.1002/anie.201204003
n12:organizacniJednotka
11310