Home / Publications / α-Pentafluoroethylated amines: a new synthetic approach

α-Pentafluoroethylated amines: a new synthetic approach

Martin Holger Königsmann 1, 2
Martin Holger Königsmann
Enno Lork 2
Enno Lork
Irina Leonovna Odinets 3
Irina Leonovna Odinets
Valentin Georgievich Nenajdenko
Nikolaj Evgenievich Shevchenko 4
Nikolaj Evgenievich Shevchenko
Gerd-Volker Röschenthaler 2
Gerd-Volker Röschenthaler
Published 2006-07-06
CommunicationVolume 16, Issue 3, 141-143
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Königsmann M. H. et al. α-Pentafluoroethylated amines: a new synthetic approach // Mendeleev Communications. 2006. Vol. 16. No. 3. pp. 141-143.
GOST all authors (up to 50) Copy
Königsmann M. H., Lork E., Odinets I. L., Nenajdenko V. G., Shevchenko N. E., Röschenthaler G. α-Pentafluoroethylated amines: a new synthetic approach // Mendeleev Communications. 2006. Vol. 16. No. 3. pp. 141-143.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2006v016n03ABEH002348
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002348
TI - α-Pentafluoroethylated amines: a new synthetic approach
T2 - Mendeleev Communications
AU - Königsmann, Martin Holger
AU - Lork, Enno
AU - Odinets, Irina Leonovna
AU - Nenajdenko, Valentin Georgievich
AU - Shevchenko, Nikolaj Evgenievich
AU - Röschenthaler, Gerd-Volker
PY - 2006
DA - 2006/07/06
PB - Mendeleev Communications
SP - 141-143
IS - 3
VL - 16
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2006_Königsmann,
author = {Martin Holger Königsmann and Enno Lork and Irina Leonovna Odinets and Valentin Georgievich Nenajdenko and Nikolaj Evgenievich Shevchenko and Gerd-Volker Röschenthaler},
title = {α-Pentafluoroethylated amines: a new synthetic approach},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002348},
number = {3},
pages = {141--143},
doi = {10.1070/MC2006v016n03ABEH002348}
}
MLA
Cite this
MLA Copy
Königsmann, Martin Holger, et al. “α-Pentafluoroethylated amines: a new synthetic approach.” Mendeleev Communications, vol. 16, no. 3, Jul. 2006, pp. 141-143. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002348.

Abstract

Pentafluoroethyllithium generated from pentafluoroethane and n-butyl lithium added to selected imines, which were activated using BF3 etherate, furnished α-pentafluoroethylated amines and, unexpectedly, depending on the stoichiometry of the reactants, bis(pentafluoroethyl)fluoro-N-(isopropyl)diisopropyliminium borate, whose molecular structure was confirmed by X-ray diffraction.

References

1.
10.1070/MC2006v016n03ABEH002348_bib1
Kirsch
Modern Fluoroorganic Chemistry, 2004
2.
10.1070/MC2006v016n03ABEH002348_bib2
Bégué
Chimie bioorganique et médicinale du fluor, 2005
3.
10.1070/MC2006v016n03ABEH002348_bib3_1
Becker
Inventory of Industrial Fluoro-Biochemicals, 1997
4.
10.1070/MC2006v016n03ABEH002348_bib3_2
Welch
Fluorine in Bioorganic Chemistry, 1991
5.
Trifluoroethylamines as amide isosteres in inhibitors of cathepsin K
Black W.C., Bayly C.I., Davis D.E., Desmarais S., Falgueyret J., Léger S., Li C.S., Massé F., McKay D.J., Palmer J.T., Percival M.D., Robichaud J., Tsou N., Zamboni R.
Bioorganic and Medicinal Chemistry Letters, 2005
6.
New fluorinated pyrrolidine and azetidine amides as dipeptidyl peptidase IV inhibitors
Hulin B., Cabral S., Lopaze M.G., Van Volkenburg M.A., Andrews K.M., Parker J.C.
Bioorganic and Medicinal Chemistry Letters, 2005
7.
Facile synthesis of 1,1-gem-dialkylperfluoroalkylamines
Zhang N., Ayral-Kaloustian S.
Journal of Fluorine Chemistry, 2002
10.
Boron trifluoride-assisted perfluoroalkylation of carbon-nitrogen double bonds
Uno H., Okada S., Ono T., Shiraishi Y., Suzuki H.
Journal of Organic Chemistry, 1992
11.
Nucleophilic addition of the pentafluoroethyl group to aldehydes, ketones, and esters
12.
Solution and Solid-State Characteristics of Imine Adducts with Tris(pentafluorophenyl)borane
Blackwell J.M., Piers W.E., Parvez M., McDonald R.
Organometallics, 2002
13.
M. Schneider, A. Marhold, A. Kolomeitsev, A. Kadyrov, G.-V. Röschenthaler and J. Barten. Patent 2002, DE 10128703, EP 1266902; 2003, JP 2003055385, US 2003065135; 2005, US 6872861.
14.
Polyfluoroorganotrifluoroborates and -difluoroboranes: interesting materials in fluoroorgano and fluoroorgano-element chemistry
Abo-Amer A., Adonin N.Y., Bardin V.V., Fritzen P., Frohn H., Steinberg C.
Journal of Fluorine Chemistry, 2004
15.
Novel heterocycles from alkylamino-bis(trifluoromethyl) borane, (CF3)2BNR2, and isocyanides. Crystal and molecular structure of (NC)(CF3)2B · NHMe2,
Ansorge A., Brauer D.J., Buchheim-Spiegel S., Burger H., Hagen T., Pawelke G.
Journal of Organometallic Chemistry, 1995
16.
Exchange reactions of tris(dimethylamino)phosphine and arsine with perfluoroalkyl iodides
Ang H.G., Manoussakis G., El-Nigumi Y.O.
Journal of Inorganic and Nuclear Chemistry, 1968