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Chemistry Seminar Series: Martin Oestreich​Export this event to calendar

Friday, June 2, 2017 — 2:30 PM EDT

Seemingly simple reactions with silicon

Martin Oestreich​, Professor, Institut für Chemie
Technische Universität Berlin, Germany 


Room:  C2 361 (Reading Room)
Host:  Eric Fillion

Abstract:  This talk tells the story of how our work on tamed silicon cations1–3 led us to introduce the new concept of transfer hydrosilylation,4 even with monosilane!5  The electron-deficient boron Lewis acid tris(pentafluorophenyl)borane catalyzes the release of hydrosilanes from cyclohexa-2,5-dien-1-yl-substituted silanes.  The same boron catalyst will then activate the Si-H bond for the reaction with representative pi- and sigma-donating substrates.  The net transformation is a transfer hydrosilylation.

The catalytic generation of silicenium ions by cooperative Si-H bond activation will also be presented, including a detailed mechanistic analysis of the heterolytic Si-H bond cleavage.6  The new catalytic entry into these main-group electrophiles is of broad synthetic utility as highlighted by inter- and intramolecular electrophilic C-H bond silylation.7 Moreover, additional approaches to Friedel-Crafts-type C-H silylation8 either using base-metals salts9 or just protons10 as promoters will be discussed.

  1. H. F. T. Klare, K. Bergander, M. Oestreich, Angew. Chem. Int. Ed. 2009, 48, 9077 - 9079; R. K. Schmidt, K. Müther, C. Mück-Lichtenfeld, S. Grimme, M. Oestreich, J. Am. Chem. Soc. 2012, 134, 4421 - 4428.
  2. K. Müther, R. Fröhlich, C. Mück-Lichtenfeld, S. Grimme, M. Oestreich, J. Am. Chem. Soc. 2011, 133, 12442 - 12444; K. Müther, P. Hrobárik, V. Hrobáriková, M. Kaupp, M. Oestreich, Chem. Eur. J. 2013, 19, 16579 - 16594.
  3. A. Simonneau, T. Biberger, M. Oestreich, Organometallics 2015, 34, 3927 - 3929.
  4. M. Oestreich, Angew. Chem. Int. Ed. 2016, 55, 494 - 499.
  5. A. Simonneau, M. Oestreich, Angew. Chem. Int. Ed. 2013, 52, 11905 - 11907; S. Keess, A. Simonneau, M. Oestreich, Organometallics 2015, 34, 790 - 799; A. Simonneau, M. Oestreich, Nat. Chem. 2015, 7, 816 - 822.
  6. T. Stahl, P. Hrobárik, C. D. F. Königs, Y. Ohki, K. Tatsumi, S. Kemper, M. Kaupp, H. F. T. Klare, M. Oestreich, Chem. Sci. 2015, 6, 4324 - 4334.
  7. H. F. T. Klare, M. Oestreich, J.-i. Ito, H. Nishiyama, Y. Ohki, K. Tatsumi, J. Am. Chem. Soc. 2011, 133, 3312 - 3315; L. Omann, M. Oestreich, Angew. Chem. Int. Ed. 2015, 54, 10276 – 10279; L. Omann, M. Oestreich, Organometallics DOI: 10.1021/acs.organomet.6b00801.
  8. S. Bähr, M. Oestreich, Angew. Chem. Int. Ed. DOI: 10.1002/anie.201608470.
  9. Q. Yin, H. F. T. Klare, M. Oestreich, Angew. Chem. Int. Ed. 2016, 55, 3204 - 3207.
  10. Q.-A. Chen, H. F. T. Klare, M. Oestreich, J. Am. Chem. Soc. 2016, 138, 7868 - 7871.

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