Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations
Тип публикации: Journal Article
Дата публикации: 2014-08-21
scimago Q1
wos Q1
БС1
SJR: 5.3
CiteScore: 26.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
25146595
General Chemistry
Catalysis
Краткое описание
The trifluoromethanide anion is the postulated key intermediate in nucleophilic trifluoromethylation reactions. However, for more than six decades, the trifluoromethanide anion was widely believed to exist only as a short-lived transient species in the condensed phase. It has now been prepared in bulk for the first time in THF solution. The trifluoromethanide anion with the [K(18-crown-6)](+) cation was unequivocally characterized by low-temperature (19)F and (13)C NMR spectroscopy. Its intermediacy in nucleophilic trifluoromethylation reactions was directly evident by its reaction chemistry with various electrophilic substrates. Variable-temperature NMR spectroscopy, along with quantum mechanical calculations, support the persistence of the trifluoromethanide anion.
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Vijaya Prakash G. et al. Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations // Angewandte Chemie - International Edition. 2014. Vol. 53. No. 43. pp. 11575-11578.
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Vijaya Prakash G., Wang F., Zhang Z., Haiges R., Rahm M., Christe K. O., Mathew T., Olah G. Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations // Angewandte Chemie - International Edition. 2014. Vol. 53. No. 43. pp. 11575-11578.
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TY - JOUR
DO - 10.1002/anie.201406505
UR - https://doi.org/10.1002/anie.201406505
TI - Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations
T2 - Angewandte Chemie - International Edition
AU - Vijaya Prakash, G.
AU - Wang, Fang
AU - Zhang, Zhe
AU - Haiges, Ralf
AU - Rahm, Martin
AU - Christe, Karl O.
AU - Mathew, Thomas
AU - Olah, George
PY - 2014
DA - 2014/08/21
PB - Wiley
SP - 11575-11578
IS - 43
VL - 53
PMID - 25146595
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2014_Vijaya Prakash,
author = {G. Vijaya Prakash and Fang Wang and Zhe Zhang and Ralf Haiges and Martin Rahm and Karl O. Christe and Thomas Mathew and George Olah},
title = {Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations},
journal = {Angewandte Chemie - International Edition},
year = {2014},
volume = {53},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/anie.201406505},
number = {43},
pages = {11575--11578},
doi = {10.1002/anie.201406505}
}
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MLA
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Vijaya Prakash, G., et al. “Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations.” Angewandte Chemie - International Edition, vol. 53, no. 43, Aug. 2014, pp. 11575-11578. https://doi.org/10.1002/anie.201406505.