Fluoride complexation by bidentate silicon Lewis acids

Horstmann J, Niemann M, Berthold K-N, Mix A, Neumann B, Stammler H-G, Mitzel NW (2017)
DALTON TRANSACTIONS 46(6): 1898-1913.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Horstmann, JanUniBi; Niemann, Mark; Berthold, Katar-Na; Mix, AndreasUniBi; Neumann, BeateUniBi; Stammler, Hans-GeorgUniBi; Mitzel, Norbert W.UniBi
Einrichtung
Fakultät für Chemie > Anorganische Chemie und Strukturchemie
Abstract / Bemerkung
Diethynyldiphenylsilane (1) and divinyldiphenylsilane (2) were functionalized by hydrosilylation reactions with HSiMe2Cl, HSiMeCl2 and HSiCl3. Fluorination of the resulting compounds generates bidentate openchain Lewis acids of increasing acidity. All semi-flexible [Ph2Si(CH=CHSiFnMe3-n)(2) (n = 1, 2, 3)] and flexible [Ph2Si(CH2 CH2SiFnMe3-n)(2) (n = 1, 2, 3)] bidentate Lewis acids were obtained in good to excellent yields. The different fluoride ion complexation behavior was explored in detail by multinuclear (low temperature) NMR spectroscopy. The Lewis acidic bidentate molecules as well as the resulting mono- and bissilicates were completely characterized by NMR spectroscopy, mass spectrometry and in part by elemental analysis and X- ray diffraction experiments.
Erscheinungsjahr
2017
Zeitschriftentitel
DALTON TRANSACTIONS
Band
46
Ausgabe
6
Seite(n)
1898-1913
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2910350

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Horstmann J, Niemann M, Berthold K-N, et al. Fluoride complexation by bidentate silicon Lewis acids. DALTON TRANSACTIONS. 2017;46(6):1898-1913.
Horstmann, J., Niemann, M., Berthold, K. - N., Mix, A., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2017). Fluoride complexation by bidentate silicon Lewis acids. DALTON TRANSACTIONS, 46(6), 1898-1913. doi:10.1039/c6dt04608h
Horstmann, Jan, Niemann, Mark, Berthold, Katar-Na, Mix, Andreas, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. 2017. “Fluoride complexation by bidentate silicon Lewis acids”. DALTON TRANSACTIONS 46 (6): 1898-1913.
Horstmann, J., Niemann, M., Berthold, K. - N., Mix, A., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2017). Fluoride complexation by bidentate silicon Lewis acids. DALTON TRANSACTIONS 46, 1898-1913.
Horstmann, J., et al., 2017. Fluoride complexation by bidentate silicon Lewis acids. DALTON TRANSACTIONS, 46(6), p 1898-1913.
J. Horstmann, et al., “Fluoride complexation by bidentate silicon Lewis acids”, DALTON TRANSACTIONS, vol. 46, 2017, pp. 1898-1913.
Horstmann, J., Niemann, M., Berthold, K.-N., Mix, A., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Fluoride complexation by bidentate silicon Lewis acids. DALTON TRANSACTIONS. 46, 1898-1913 (2017).
Horstmann, Jan, Niemann, Mark, Berthold, Katar-Na, Mix, Andreas, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Fluoride complexation by bidentate silicon Lewis acids”. DALTON TRANSACTIONS 46.6 (2017): 1898-1913.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

From Bidentate Gallium Lewis Acids to Supramolecular Complexes.
Horstmann J, Hyseni M, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 56(22), 2017
PMID: 28418175
Organotin-based receptors for anions and ion pairs.
Naseer MM, Jurkschat K., Chem Commun (Camb) 53(58), 2017
PMID: 28580478

76 References

Daten bereitgestellt von Europe PubMed Central.


Pedersen, J. Am. Chem. Soc. 89(), 1967

Lamm, Eur. J. Inorg. Chem. (), 2014
Dialkylaluminium-, -gallium-, and -indium-based poly-Lewis acids with a 1,8-diethynylanthracene backbone.
Chmiel J, Neumann B, Stammler HG, Mitzel NW., Chemistry 16(39), 2010
PMID: 20827789

Antonisse, Chem. Commun. (), 1998
Coordination and organometallic compounds as anion receptors and sensors.
Steed JW., Chem Soc Rev 38(2), 2008
PMID: 19169464
Anion Recognition and Sensing: The State of the Art and Future Perspectives.
Beer PD, Gale PA., Angew. Chem. Int. Ed. Engl. 40(3), 2001
PMID: 11180358
Fluoride ion complexation and sensing using organoboron compounds.
Wade CR, Broomsgrove AE, Aldridge S, Gabbai FP., Chem. Rev. 110(7), 2010
PMID: 20540560
Fluoride ion recognition by chelating and cationic boranes.
Hudnall TW, Chiu CW, Gabbai FP., Acc. Chem. Res. 42(2), 2009
PMID: 19140747

Zhao, Organometallics 31(), 2012

Li, MedChemComm 3(), 2012

Koomen, Int. J. Mass Spectrom. 225(), 2003
A bidentate Lewis acid with a telluronium ion as an anion-binding site.
Zhao H, Gabbai FP., Nat Chem 2(11), 2010
PMID: 20966957
Squeezing fluoride out of water with a neutral bidentate antimony(V) Lewis acid.
Hirai M, Gabbai FP., Angew. Chem. Int. Ed. Engl. 54(4), 2014
PMID: 25424599

Jones, Organometallics 34(), 2015

Hirai, Organometallics 35(), 2016

Brondani, Angew. Chem., Int. Ed. Engl. 35(), 1996

Jung, Tetrahedron Lett. 29(), 1988

Tamao, Organometallics 11(), 1992

Aoyagi, J. Chem. Soc., Perkin. Trans. 2 (), 1994

Altmann, Organometallics 19(), 2000

Tamao, J. Organomet. Chem. 506(), 1996
Synthesis and anion affinity of a bidendate sulfonium fluorosilane Lewis acid.
Kim Y, Kim M, Gabbai FP., Org. Lett. 12(3), 2010
PMID: 20052988
Synthesis of B/Si bidentate Lewis acids, o-(Fluorosilyl)(dimesitylboryl)benzenes, and their fluoride ion affinity.
Kawachi A, Tani A, Shimada J, Yamamoto Y., J. Am. Chem. Soc. 130(13), 2008
PMID: 18327943

Dakternieks, Organometallics 17(), 1998
Hydrogen- and fluorine-bridged disilyl cations and their use in catalytic C-F activation.
Panisch R, Bolte M, Muller T., J. Am. Chem. Soc. 128(30), 2006
PMID: 16866520

Dorsey, Organometallics 27(), 2008

Dakternieks, Organometallics 16(), 1997
Silicon- and Tin-Containing Open-Chain and Eight-Membered-Ring Compounds as Bicentric Lewis Acids toward Anions.
Wendji AS, Dietz C, Kuhn S, Lutter M, Schollmeyer D, Hiller W, Jurkschat K., Chemistry 22(1), 2015
PMID: 26616743

Weisheim, Z. Anorg. Allg. Chem. 642(), 2016
Tridentate Lewis acids with phenyl substituted 1,3,5-trisilacyclohexane backbones.
Weisheim E, Bucker L, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 45(1), 2016
PMID: 26599621
Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry.
Weisheim E, Reuter CG, Heinrichs P, Vishnevskiy YV, Mix A, Neumann B, Stammler HG, Mitzel NW., Chemistry 21(35), 2015
PMID: 26213228

Weisheim, Z. Naturforsch., B: Chem. Sci. 71(), 2016
1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures.
Lamm JH, Horstmann J, Stammler HG, Mitzel NW, Zhabanov YA, Tverdova NV, Otlyotov AA, Giricheva NI, Girichev GV., Org. Biomol. Chem. 13(33), 2015
PMID: 26204511

Nieland, Z. Anorg. Allg. Chem. 640(), 2014
Polyalkynylanthracenes--syntheses, structures and their behaviour towards UV irradiation.
Lamm JH, Glatthor J, Weddeling JH, Mix A, Chmiel J, Neumann B, Stammler HG, Mitzel NW., Org. Biomol. Chem. 12(37), 2014
PMID: 25162922

Weisheim, Eur. J. Inorg. Chem. 16(), 2016

Krüerke, J. Organomet. Chem. 21(), 1970

Rosenberg, J. Org. Chem. 22(), 1957

Fischer, Organometallics 32(), 2013
Covalent radii revisited.
Cordero B, Gomez V, Platero-Prats AE, Reves M, Echeverria J, Cremades E, Barragan F, Alvarez S., Dalton Trans (21), 2008
PMID: 18478144

Holleman, 1985

Dierker, Adv. Synth. Catal. 351(), 2009

Anisimov, J. Organomet. Chem. 772(), 2014

Carr, J. Mater. Chem. 7(), 1997

Mitzel, Z. Naturforsch. 57B(), 2002
The experimental gas-phase structures of 1,3,5-trisilylbenzene and hexasilylbenzene and the theoretical structures of all benzenes with three or more silyl substituents.
Johnston BF, Mitzel NW, Rankin DW, Robertson HE, Rudinger C, Schmidbaur H., Dalton Trans (13), 2005
PMID: 15962050

Laska, Organometallics 17(), 1998
(Dimethylaminomethyl)trifluorosilane, Me2NCH2SiF3--a model for the alpha-effect in aminomethylsilanes.
Mitzel NW, Vojinovic K, Foerster T, Robertson HE, Borisenko KB, Rankin DW., Chemistry 11(17), 2005
PMID: 15991212

Menshutkin, Zh. Russ. Fiz. Khim. Ova. Chast. Khim. 43(), 1911

Smith, J. Chem. Soc. Trans. 41(), 1882

Peyronel, Gazz. Chim. Ital. 98(), 1968

Bombieri, Inorg. Chim. Acta 6(), 1972

Demalde, Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. 28(), 1972

Szyamnski, Acta. Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 28(), 1969

Pohl, Angew. Chem. 99(), 1987

Schmidbaur, Organometallics 6(), 1987
Colour Reactions Attributed to Vitamin A.
Carr FH, Price EA., Biochem. J. 20(3), 1926
PMID: 16743683

Plack, J. Organomet. Chem. 553(), 1998

Sakurai, J. Am. Chem. Soc. 104(), 1982

Rani, Polyhedron 26(), 2007

Pietschnig, Chem. Commun. (), 2001

Chuit, Chem. Rev. 93(), 1993

Damrauer, Organometallics 5(), 1989
Exploring the anion-cation interaction in m-terphenyltetrafluorosilicates by using multinuclear NMR spectroscopy, X-ray diffraction, and ICR-FT-MS.
Spirk S, Belaj F, Nieger M, Kofeler H, Rechberger GN, Pietschnig R., Chemistry 15(37), 2009
PMID: 19681072

Johnson, Inorg. Chem. 28(), 1989

Damrauer, Organometallics 5(), 1986

Yamaguchi, Organometallics 18(), 1999
Hypervalent hydridosilicates: synthesis, structure and hydride bridging.
Prince PD, Bearpark MJ, McGrady GS, Steed JW., Dalton Trans (2), 2007
PMID: 18097494

Schomburg, J. Organomet. Chem. 221(), 1981

Ou, Inorg. Chem. 36(), 1997

Ebata, J. Am. Chem. Soc. 116(), 1994
Comparison of Phosphorus and Silicon: Hypervalency, Stereochemistry, and Reactivity.
Holmes RR., Chem. Rev. 96(3), 1996
PMID: 11848776

Dietrich, Tetrahedron Lett. 15(), 1973

Yamaguchi, J. Am. Chem. Soc. 122(), 2000

Dolomanov, J. Appl. Crystallogr. 42(), 2009
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
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