302
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

The reactivity of an NHC-stabilized silicon(II) hydride

&
Pages 605-608 | Received 03 Dec 2015, Accepted 03 Dec 2015, Published online: 06 Apr 2016

References

  • Denk, M.; Lennon, R.; Hayashi, R.; West, R.; Belyakov, A. V.; Verne, H. P.; Haaland, A.; Wagner, M.; Meltzer, N. J. Am. Chem. Soc. 1994, 116, 2691–2692.
  • Mizuhata, Y.; Sasamori, T.; Tokitoh, N. Chem. Rev. 2009, 109, 3479–3511.
  • Asay, M.; Jones, C.; Driess, M. Chem. Rev. 2011, 111, 354–396.
  • Inoue, S.; Driess, M. Science of Synthesis Knowledge Updates, 1 ed.; Thieme: Stuttgart, 2012 Vol. 4; 213–295.
  • Jana, A.; Leusser, D.; Objartel, I.; Roesky, H. W.; Stalke, D. Dalton Trans. 2011, 40, 5458–5463.
  • Blom, B.; Driess, M.; Gallego, D.; Inoue, S. Chem. Eur. J. 2012, 18, 13355–13360.
  • Blom, B.; Enthaler, S.; Inoue, S.; Irran, E.; Driess, M. J. Am. Chem. Soc. 2013, 135, 6703–6713.
  • Jungton, A. -K.; Meltzer, A.; Präsang, C.; Braun, T.; Driess M.; Penner, A. Dalton Trans. 2010, 39, 5436–5438.
  • Stoelzel, M.; Präsang, C.; Inoue, S.; Enthaler, S.; Driess, M. Angew. Chem., Int. Ed. 2012, 51, 399–403.
  • Abraham, M. Y.; Wang, Y.; Xie, Y.; Wei, P.; Schaefer III, H. F.; Schleyer, P. V. R.; Robinson, G. J. Am. Chem. Soc. 2011, 133, 8874–8876.
  • Al-Rafia, S. M. I.; Malcom, A. C.; McDonald, R.; Ferguson, M. J.; Rivard, E. Chem. Commun. 2012, 48, 1308–1310.
  • Rodriguez, R.; Gau, D.; Contie, Y.; Kato, T.; Saffon-Merceron, N.; Baceiredo, A. Angew. Chem., Int. Ed. 2011, 50, 11492–11495.
  • Inoue, S.; Eisenhut, C. J. Am. Chem. Soc. 2013, 135, 18315–18318.
  • Eisenhut, C.; Szilvási, T.; Breit, N. C.; Inoue, S. Chem. Eur. J. 2015, 21, 1949–1954.
  • Agou, T.; Sugiyama, Y.; Sasamori, T.; Sakai, H.; Furukawa, Y.; Takagi, N.; Guo, J.-D.; Nagase, S.; Hashizume, D.; Tokitoh, N. J. Am. Chem. Soc. 2012, 134, 4120–4123.
  • Lebedev, Y. N.; Das, U.; Chernov, O.; Schnakenburg, G.; Filippou, A. C. Chem. Eur. J. 2014, 20, 9280–9289.
  • Gao, Y.; Zhang, J.; Hu, H.; Cui, C. Organometallics 2010, 29, 3063–3065.
  • Crystal data for 6 at 150 K: C37H66N4Si3, MW = 651.21, Triclinic, space group P-1, a = 8.4799(3) Å, b = 12.7150(5) Å, c = 18.5396(7) Å, α = 99.648(3), β = 91.221(3), γ = 98.838(3), V = 1945.03(13) Å3, Z = 2, Dcalc = 1.112 g cm−3. R = 0.0532 (I >2σ(I)), wR (all data) = 0.1528. GOF = 1.039. CCDC-1419674.
  • NMR data of 6: 1H NMR (200 MHz, C6D6, 298 K): δ [ppm] = 0.33 (s, 9 H, Si(CH3)3), 1.13 (s, 3 H, C = C-CH3), 1.29 (s, 27 H, Si(C(CH3)3)), 1.55 (s, 6 H, C = C-CH3), 1.81 (s, 3 H, C = C-CH3), 2.68–3.17 (br, 6 H, N-CH3), 3.09 (d, 2JHH = 3 Hz, 1 H, Si-CH-Si(CH3)3), 3. 33 (s, 3 H, N-CH3), 3.80 (d, 2JHH = 15 Hz, 1 H, CH2), 4.25 (d, 2JHH = 15 Hz, 1 H, CH2), 5.02 (d, 2JHH = 3 Hz, 1JSiH-satellite = 162 Hz, 1 H, Si-H), 6.74 – 7.43 (m, 5 H, Ph-H). 13C{1H} NMR (100.61 MHz, C6D6, 298 K) δ; [ppm] = 3.7 (Si-CH-Si), 4.2 (Si(CH3)3), 8.8, 8.9, 9.0, 9.3 (CH3-C = C-CH3), 24.4 (C(CH3)3), 32.4 (C(CH3)3), 34.3, 32.0 (N-CH3), 35.1 (N-CH2-Si), 74.6 (C = C(Ph)), 117.7 (C = CN2), 122.5, 123.3, 123.9 (CH3-C = C-CH3), 129.3, 146.9, 151.7, (C-Ph), 210.7 (:CN2). 29Si{1H} NMR (79.49 MHz, C6D6, 298 K): δ [ppm] = −32.5 (Si-H), 7.4 (SiMe3), 11.5 (SitBu3). HR MS (APCI): m/z (%) = Calcd. for C37H67N4Si4O 667.4617 (1, [M+OH]+), found 667.4611.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.