| JASÍKOVÁ, Lucie, Maitê RODRIGUES, Jana LAPEŠOVÁ, Tomáš LÍZAL, Vladimír ŠINDELÁŘ and Jana ROITHOVÁ. Bambusurils as a mechanistic tool for probing anion effects. FARADAY DISCUSSIONS. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2019, vol. 220, DEC, p. 58-70. ISSN 1359-6640. Available from: https://dx.doi.org/10.1039/C9FD00038K. |
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@article{1561376,
author = {Jasíková, Lucie and Rodrigues, Maitê and Lapešová, Jana and Lízal, Tomáš and Šindelář, Vladimír and Roithová, Jana},
article_location = {CAMBRIDGE},
article_number = {DEC},
doi = {http://dx.doi.org/10.1039/C9FD00038K},
keywords = {N-HETEROCYCLIC CARBENES; GOLD(I)-CATALYZED HYDROALKOXYLATION; MASS-SPECTROMETRY; COUNTERION; ALKOXYLATION; ALKYNES; HYDROPHENOXYLATION; HYDROGENATION; CATALYSIS; COMPLEXES},
language = {eng},
issn = {1359-6640},
journal = {FARADAY DISCUSSIONS},
title = {Bambusurils as a mechanistic tool for probing anion effects},
url = {https://pubs.rsc.org/en/content/articlelanding/2019/FD/C9FD00038K#!divAbstract},
volume = {220},
year = {2019}
}
TY - JOUR
ID - 1561376
AU - Jasíková, Lucie - Rodrigues, Maitê - Lapešová, Jana - Lízal, Tomáš - Šindelář, Vladimír - Roithová, Jana
PY - 2019
TI - Bambusurils as a mechanistic tool for probing anion effects
JF - FARADAY DISCUSSIONS
VL - 220
IS - DEC
SP - 58-70
EP - 58-70
PB - ROYAL SOC CHEMISTRY
SN - 13596640
KW - N-HETEROCYCLIC CARBENES
KW - GOLD(I)-CATALYZED HYDROALKOXYLATION
KW - MASS-SPECTROMETRY
KW - COUNTERION
KW - ALKOXYLATION
KW - ALKYNES
KW - HYDROPHENOXYLATION
KW - HYDROGENATION
KW - CATALYSIS
KW - COMPLEXES
UR - https://pubs.rsc.org/en/content/articlelanding/2019/FD/C9FD00038K#!divAbstract
L2 - https://pubs.rsc.org/en/content/articlelanding/2019/FD/C9FD00038K#!divAbstract
N2 - Bambusuril macrocycles have high affinity towards anions (X-) such as PF6- and SbF6- or BF4- and ClO4-. Therefore, addition of bambusurils to reaction mixtures containing these anions effectively removes the free anions from the reaction process. Hence, comparing reactions with and without addition of bambusurils can demonstrate whether the anions actively participate in the reaction mechanism or not. We show this approach for gold(I) mediated addition of methanol to an alkyne. The reaction mechanism can proceed via monoaurated intermediates (e.g., in catalysis with [(IPr)AuX]) or via diaurated intermediates (e.g., in catalysis with [(PPh3)AuX]). We show that anions X- slightly affect the reaction rates, however the effect stays almost the same even after their encapsulation in the cavity of bambusurils. We also demonstrate that X- affects the overall reaction rate in the very same way as the reaction rate of the protodeauration step. All results are consistent with the indirect effect of X- by the acidity of the conjugated acid HX on the rate-determining step. There is no evidence that a direct involvement of X- would affect the reaction rate.
ER -
JASÍKOVÁ, Lucie, Maitê RODRIGUES, Jana LAPEŠOVÁ, Tomáš LÍZAL, Vladimír ŠINDELÁŘ and Jana ROITHOVÁ. Bambusurils as a mechanistic tool for probing anion effects. \textit{FARADAY DISCUSSIONS}. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2019, vol.~220, DEC, p.~58-70. ISSN~1359-6640. Available from: https://dx.doi.org/10.1039/C9FD00038K.
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