The Trifluoromethyl Anion

Anton Lishchynskyi; Fedor M. Miloserdov; Eddy Martin; Jordi Benet-Buchholz; Eduardo C. Escudero-Adán; Andrey I. Konovalov; Vladimir V. Grushin

doi:10.1002/anie.201507356

The Trifluoromethyl Anion

Anton Lishchynskyi, Fedor M. Miloserdov, Eddy Martin, Jordi Benet-Buchholz, Eduardo C. Escudero-Adán, Andrey I. Konovalov, Vladimir V. Grushin

Research output: Contribution to journal › Article › Academic › peer-review

35 Citations (Scopus)

Abstract

First evidence for the existence of free trifluoromethyl anion CF₃^- has been obtained. The 3D-caged potassium cation in [K(crypt-222)]⁺ is inaccessible to CF₃^-, thus rendering it uncoordinated ("naked"). Ionic [K(crypt-222)]⁺ CF₃^- has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations, and reactivity toward electrophiles.

Original language	English
Pages (from-to)	15289-15293
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	50
DOIs	https://doi.org/10.1002/anie.201507356
Publication status	Published - 7 Dec 2015
Externally published	Yes

Keywords

carbanions
NMR spectroscopy
trifluoromethyl anion
trifluoromethylation
X-ray diffraction

Access to Document

10.1002/anie.201507356

Cite this

@article{07b28fe90d00411bb4909b5448f57ccb,

title = "The Trifluoromethyl Anion",

abstract = "First evidence for the existence of free trifluoromethyl anion CF3- has been obtained. The 3D-caged potassium cation in [K(crypt-222)]+ is inaccessible to CF3-, thus rendering it uncoordinated ({"}naked{"}). Ionic [K(crypt-222)]+ CF3- has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations, and reactivity toward electrophiles.",

keywords = "carbanions, NMR spectroscopy, trifluoromethyl anion, trifluoromethylation, X-ray diffraction",

author = "Anton Lishchynskyi and Miloserdov, \{Fedor M.\} and Eddy Martin and Jordi Benet-Buchholz and Escudero-Ad{\'a}n, \{Eduardo C.\} and Konovalov, \{Andrey I.\} and Grushin, \{Vladimir V.\}",

year = "2015",

month = dec,

day = "7",

doi = "10.1002/anie.201507356",

language = "English",

volume = "54",

pages = "15289--15293",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "VCH",

number = "50",

}

TY - JOUR

T1 - The Trifluoromethyl Anion

AU - Lishchynskyi, Anton

AU - Miloserdov, Fedor M.

AU - Martin, Eddy

AU - Benet-Buchholz, Jordi

AU - Escudero-Adán, Eduardo C.

AU - Konovalov, Andrey I.

AU - Grushin, Vladimir V.

PY - 2015/12/7

Y1 - 2015/12/7

N2 - First evidence for the existence of free trifluoromethyl anion CF3- has been obtained. The 3D-caged potassium cation in [K(crypt-222)]+ is inaccessible to CF3-, thus rendering it uncoordinated ("naked"). Ionic [K(crypt-222)]+ CF3- has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations, and reactivity toward electrophiles.

AB - First evidence for the existence of free trifluoromethyl anion CF3- has been obtained. The 3D-caged potassium cation in [K(crypt-222)]+ is inaccessible to CF3-, thus rendering it uncoordinated ("naked"). Ionic [K(crypt-222)]+ CF3- has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations, and reactivity toward electrophiles.

KW - carbanions

KW - NMR spectroscopy

KW - trifluoromethyl anion

KW - trifluoromethylation

KW - X-ray diffraction

U2 - 10.1002/anie.201507356

DO - 10.1002/anie.201507356

M3 - Article

AN - SCOPUS:84955182137

SN - 1433-7851

VL - 54

SP - 15289

EP - 15293

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 50

ER -

The Trifluoromethyl Anion

Abstract

Keywords

Access to Document

Fingerprint

Cite this