Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane

Wiesemann M, Niemann M, Kloesener J, Neumann B, Stammler H-G, Hoge B (2018)
CHEMISTRY-A EUROPEAN JOURNAL 24(11): 2699-2708.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
A versatile two-step synthesis of tris(pentafluoroethyl)stannane, HSn(C2F5)(3), is presented. Electron-withdrawing C2F5 groups significantly influence the polarity of the tin-hydrogen bond, which allows facile deprotonation of the compound, even in water. The utility of this electron-deficient stannane was illustrated in hydrostannylations of alkenes and alkynes, as well as in dehalogenation reactions. The remarkably high reactivity of HSn(C2F5)(3) is demonstrated in fast hydrostannylations, even in the absence of activators, whereby the regioselectivity of this process turns out to be solvent dependent. It is of great advantage that in dehalogenation reactions volatile halogenotris(pentafluoroethyl)stannanes, XSn(C2F5)(3) (X=I, Br), are formed that allow facile separation of the tin-containing byproducts from the reaction mixtures.
Stichworte
electron-deficient compounds; fluorine; hydrides; stannanes; synthesis; design
Erscheinungsjahr
2018
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
24
Ausgabe
11
Seite(n)
2699-2708
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2918659

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Wiesemann M, Niemann M, Kloesener J, Neumann B, Stammler H-G, Hoge B. Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(11):2699-2708.
Wiesemann, M., Niemann, M., Kloesener, J., Neumann, B., Stammler, H. - G., & Hoge, B. (2018). Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane. CHEMISTRY-A EUROPEAN JOURNAL, 24(11), 2699-2708. doi:10.1002/chem.201705068
Wiesemann, Markus, Niemann, Mark, Kloesener, Johannes, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. 2018. “Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane”. CHEMISTRY-A EUROPEAN JOURNAL 24 (11): 2699-2708.
Wiesemann, M., Niemann, M., Kloesener, J., Neumann, B., Stammler, H. - G., and Hoge, B. (2018). Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane. CHEMISTRY-A EUROPEAN JOURNAL 24, 2699-2708.
Wiesemann, M., et al., 2018. Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane. CHEMISTRY-A EUROPEAN JOURNAL, 24(11), p 2699-2708.
M. Wiesemann, et al., “Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 24, 2018, pp. 2699-2708.
Wiesemann, M., Niemann, M., Kloesener, J., Neumann, B., Stammler, H.-G., Hoge, B.: Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane. CHEMISTRY-A EUROPEAN JOURNAL. 24, 2699-2708 (2018).
Wiesemann, Markus, Niemann, Mark, Kloesener, Johannes, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. “Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane”. CHEMISTRY-A EUROPEAN JOURNAL 24.11 (2018): 2699-2708.

1 Zitation 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

55 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0

Hoth, Toxicol. Ind. Health 21(), 2005

Studer, Synthesis 2002(), 2002

Baguley, Angew. Chem. Int. Ed. 37(), 1998

AUTHOR UNKNOWN, Angew. Chem. 110(), 1998

Neumann, Synthesis 1987(), 1987
Metal-mediated reductive hydrodehalogenation of organic halides.
Alonso F, Beletskaya IP, Yus M., Chem. Rev. 102(11), 2002
PMID: 12428984

Kuivila, Adv. Organomet. Chem. 1(), 1964
Metal-catalyzed hydrostannations.
Smith ND, Mancuso J, Lautens M., Chem. Rev. 100(8), 2000
PMID: 11749320

Davies, 2004

Stille, Angew. Chem. Int. Ed. Engl. 25(), 1986

AUTHOR UNKNOWN, Angew. Chem. 98(), 1986

Curran, J. Am. Chem. Soc. 121(), 1999

Sawyer, J. Am. Chem. Soc. 82(), 1960

AUTHOR UNKNOWN, 0

Bellama, Inorg. Nucl. Chem. Letters 7(), 1971

Bürger, J. Mol. Spectrosc. 121(), 1987

AUTHOR UNKNOWN, 0

Eujen, J. Organomet. Chem. 434(), 1992

Eujen, J. Organomet. Chem. 465(), 1994

Cullen, Inorg. Chem. 9(), 1970

Eujen, J. Organomet. Chem. 433(), 1992
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

Seyferth, J. Organomet. Chem. 499(), 1995

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
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
Tris(pentafluoroethyl)germane: Deprotonation and Hydrogermylation Reactions.
Pelzer S, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(50), 2017
PMID: 28256795

Westerhausen, Main Group Met. Chem. 20(), 1997

Bent, Chem. Rev. 61(), 1961

Westerhausen, J. Organomet. Chem. 411(), 1991
The Tris(pentafluoroethyl)stannate(II) Anion, [Sn(C2 F5 )3 ]- -Synthesis and Reactivity.
Wiesemann M, Klosener J, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 23(58), 2017
PMID: 28671288

Semmelhack, 1991

AUTHOR UNKNOWN, 0

Neumann, Angew. Chem. 73(), 1961

van, J. Appl. Chem. 7(), 1957

van, J. Appl. Chem. 9(), 1959

AUTHOR UNKNOWN, 0

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

AUTHOR UNKNOWN, 0

Beckwith, Tetrahedron 37(), 1981

Giese, Angew. Chem. 24(), 1985

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
SHELXT - integrated space-group and crystal-structure determination.
Sheldrick GM., Acta Crystallogr A Found Adv 71(Pt 1), 2015
PMID: 25537383
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