On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5

Wiesemann M, Klösener J, Neumann B, Stammler H-G, Hoge B (2018)
CHEMISTRY-A EUROPEAN JOURNAL 24(8): 1838-1843.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Pentafluoroethyllithium, LiC2F5, has been established as an efficient and versatile reagent for the transfer of the pentafluoroethyl unit to a number of electrophiles. Here, the stability of this species up to -40 degrees C is of advantage, particularly in comparison to its smaller congener LiCF3. The usual production of LiC2F5, however, from gaseous HC2F5 or IC2F5 and strong bases requires specially designed apparatuses, which severely impeded its value as a laboratory reagent. In this contribution we communicate an alternative gas-free and highly efficient protocol for the synthesis of LiC2F5 from the already commercialized stannate salt [PPh4][Sn(C2F5)(5)]. The [Sn(C2F5)(5)](-) anion represents not only the first example of a structurally characterized hypervalent pentaalkylstannate but also serves as a precursor for the synthesis of the homoleptic tetrakis(pentafluoroethyl)stannane, Sn(C2F5)(4). The reaction of the latter with n-butyllithium provides an insight into the mechanism of LiC2F5 generation.
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CHEMISTRY-A EUROPEAN JOURNAL
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24
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8
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1838-1843
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Wiesemann M, Klösener J, Neumann B, Stammler H-G, Hoge B. On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(8):1838-1843.
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H. - G., & Hoge, B. (2018). On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL, 24(8), 1838-1843. doi:10.1002/chem.201704807
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H. - G., and Hoge, B. (2018). On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL 24, 1838-1843.
Wiesemann, M., et al., 2018. On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL, 24(8), p 1838-1843.
M. Wiesemann, et al., “On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 24, 2018, pp. 1838-1843.
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H.-G., Hoge, B.: On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL. 24, 1838-1843 (2018).
Wiesemann, Markus, Klösener, Johannes, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. “On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5”. CHEMISTRY-A EUROPEAN JOURNAL 24.8 (2018): 1838-1843.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Pentafluoroethylated Compounds of Silicon, Germanium and Tin.
Wiesemann M, Hoge B., Chemistry 24(62), 2018
PMID: 29722451

67 References

Daten bereitgestellt von Europe PubMed Central.

Condensed-phase, halogen-bonded CF3I and C2F5I adducts for perfluoroalkylation reactions.
Sladojevich F, McNeill E, Borgel J, Zheng SL, Ritter T., Angew. Chem. Int. Ed. Engl. 54(12), 2015
PMID: 25651531

AUTHOR UNKNOWN, Angew. Chem. 127(), 2015

Ruppert, Tetrahedron Lett. 25(), 1984

Prakash, J. Am. Chem. Soc. 111(), 1989

AUTHOR UNKNOWN, 0
A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.
Morimoto H, Tsubogo T, Litvinas ND, Hartwig JF., Angew. Chem. Int. Ed. Engl. 50(16), 2011
PMID: 21442711

AUTHOR UNKNOWN, Angew. Chem. 123(), 2011
Direct cupration of fluoroform.
Zanardi A, Novikov MA, Martin E, Benet-Buchholz J, Grushin VV., J. Am. Chem. Soc. 133(51), 2011
PMID: 22136628

AUTHOR UNKNOWN, 0

Langlois, Tetrahedron Lett. 32(), 1991
Practical and innate carbon-hydrogen functionalization of heterocycles.
Fujiwara Y, Dixon JA, O'Hara F, Funder ED, Dixon DD, Rodriguez RA, Baxter RD, Herle B, Sach N, Collins MR, Ishihara Y, Baran PS., Nature 492(7427), 2012
PMID: 23201691
Radical C-H functionalization of heteroarenes under electrochemical control.
O'Brien AG, Maruyama A, Inokuma Y, Fujita M, Baran PS, Blackmond DG., Angew. Chem. Int. Ed. Engl. 53(44), 2014
PMID: 25209429

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0

Umemoto, J. Am. Chem. Soc. 115(), 1993

AUTHOR UNKNOWN, Angew. Chem. 119(), 2007

AUTHOR UNKNOWN, 0
Perfluoroalkylation with Organosilicon Reagents.
Prakash GK, Yudin AK., Chem. Rev. 97(3), 1997
PMID: 11848888
Aromatic trifluoromethylation with metal complexes.
Tomashenko OA, Grushin VV., Chem. Rev. 111(8), 2011
PMID: 21456523
A "Renaissance" in radical trifluoromethylation.
Studer A., Angew. Chem. Int. Ed. Engl. 51(36), 2012
PMID: 22890985

AUTHOR UNKNOWN, Angew. Chem. 124(), 2012
Electrophilic Perfluoroalkylating Agents.
Umemoto T., Chem. Rev. 96(5), 1996
PMID: 11848810
Long-lived trifluoromethanide anion: a key intermediate in nucleophilic trifluoromethylations.
Prakash GK, Wang F, Zhang Z, Haiges R, Rahm M, Christe KO, Mathew T, Olah GA., Angew. Chem. Int. Ed. Engl. 53(43), 2014
PMID: 25146595

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0
Acyl sulfonamides as potent protease inhibitors of the hepatitis C virus full-Length NS3 (protease-helicase/NTPase): a comparative study of different C-terminals.
Johansson A, Poliakov A, Akerblom E, Wiklund K, Lindeberg G, Winiwarter S, Danielson UH, Samuelsson B, Hallberg A., Bioorg. Med. Chem. 11(12), 2003
PMID: 12757723
Synthesis, antiprotozoal and anticancer activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles.
Andrzejewska M, Yepez-Mulia L, Cedillo-Rivera R, Tapia A, Vilpo L, Vilpo J, Kazimierczuk Z., Eur J Med Chem 37(12), 2002
PMID: 12660022

AUTHOR UNKNOWN, 0

Gassman, J. Org. Chem. 52(), 1987
(L)2 C2 P2 : Dicarbondiphosphide Stabilized by N-Heterocyclic Carbenes or Cyclic Diamido Carbenes.
Li Z, Chen X, Andrada DM, Frenking G, Benko Z, Li Y, Harmer JR, Su CY, Grutzmacher H., Angew. Chem. Int. Ed. Engl. 56(21), 2017
PMID: 28436079

AUTHOR UNKNOWN, Angew. Chem. 129(), 2017

Petrov, Tetrahedron Lett. 42(), 2001

Umemoto, J. Fluorine Chem. 20(), 1982
Nucleophilic perfluoroalkylation of aldehydes, ketones, imines, disulfides, and diselenides.
Pooput C, Dolbier WR Jr, Medebielle M., J. Org. Chem. 71(9), 2006
PMID: 16626142

Krishnamurti, J. Org. Chem. 56(), 1991

AUTHOR UNKNOWN, 0

Kolomeitsev, Tetrahedron Lett. 44(), 2003

Shevchenko, J. Fluorine Chem. 129(), 2008

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Solid-state structure of a Li/F carbenoid: pentafluoroethyllithium.
Waerder B, Steinhauer S, Neumann B, Stammler HG, Mix A, Vishnevskiy YV, Hoge B, Mitzel NW., Angew. Chem. Int. Ed. Engl. 53(43), 2014
PMID: 25205058

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Davies, 2004

Seyferth, J. Am. Chem. Soc. 83(), 1961
Pentafluoroethyl Bismuth Compounds.
Solyntjes S, Bader J, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(7), 2017
PMID: 27862439
Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2 F5 )4-n SnXn (X=Ph, Me, Cl, Br, Cp; n=1-3).
Klosener J, Wiesemann M, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 23(34), 2017
PMID: 28444920

Pfeiffer, Z. Anorg. Chem. 87(), 1914
The Tris(pentafluoroethyl)silanide Anion.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew. Chem. Int. Ed. Engl. 55(52), 2016
PMID: 27902868

AUTHOR UNKNOWN, Angew. Chem. 128(), 2016

AUTHOR UNKNOWN, 0
Synthesis and structure of pentaorganostannate having five carbon substituents.
Saito M, Imaizumi S, Tajima T, Ishimura K, Nagase S., J. Am. Chem. Soc. 129(36), 2007
PMID: 17705378
Dilithium hexaorganostannate(IV) compounds.
Schrader I, Zeckert K, Zahn S., Angew. Chem. Int. Ed. Engl. 53(50), 2014
PMID: 25314245

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

Chen, J. Fluorine Chem. 20(), 1982
Coordination Properties of Perfluoroethyl- and Perfluorophenyl-Substituted Phosphonous acids, R(f)P(OH)2.
Allefeld N, Kurscheid B, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 21(39), 2015
PMID: 26250582

Dolomanov, J. Appl. Crystallogr. 42(), 2009

AUTHOR UNKNOWN, 0
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
Crystal structure refinement with SHELXL.
Sheldrick GM., Acta Crystallogr C Struct Chem 71(Pt 1), 2015
PMID: 25567568

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