N-heterocyclic carbene-catalyzed hydrosilylation of styryl and propargylic alcohols with dihydrosilanes

Chemistry - A European Journal

Volumn 17, Issue 36, 2011, Pages 9911-9914

  Zhao, Qiwu ^a   Curran, Dennis P ^b   Malacria, Max ^a   Fensterbank, Louis ^a   Goddard, Jean Philippe ^a   Lacôte, Emmanuel ^a,c  

^a Université Pierre et Marie Curie   (France)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

carbenes; hydrogenation; hydrosilylation.; organocatalysis; silicon

Indexed keywords

CARBENES; CATALYTIC TURNOVER; HYDRIDE TRANSFERS; HYPERVALENT SILICON; N-HETEROCYCLIC; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS; PROPARGYLIC ALCOHOLS; SILYLATIONS; SYNTHETIC APPLICATION; TANDEM REACTION;

ALCOHOLS; CARBON INORGANIC COMPOUNDS; CATALYSIS; OLEFINS; REACTION KINETICS;

HYDROSILYLATION;

EID: 80051984453     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101822     Document Type: Article

References (51)

1. The Handbook of Homogeneous Hydrogenation (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007.
2. B. J. Marsh, E. L. Heath, D. R. Carbery, Chem. Commun. 2011, 47, 280
3. Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc. 2005, 127, 14544
4. S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590
5. Angew. Chem. Int. Ed. 2005, 44, 7424
6. J. B. Tuttle, S. G. Ouellet, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 12662
7. M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765
8. Angew. Chem. Int. Ed. 2006, 45, 3683; for a metal-free hydrosilylation, see
9. R. Shchepin, C. Xu, P. Dussault, Org. Lett. 2010, 12, 4772
10. D. J. Parks, J. M. Blackwell, W. E. Piers, J. Org. Chem. 2000, 65, 3090
11. L. Ilies, H. Tsuji, E. Nakamura, Org. Lett. 2009, 11, 3966.
12. K. Nozaki, Y. Aramaki, M. Yamashita, S.-H. Ueng, M. Malacria, E. Lacôte, D. P. Curran, J. Am. Chem. Soc. 2010, 132, 11449
13. J. Monot, A. Solovyev, H. Dubarle, E. Derat, D. P. Curran, M. Robert, L. Fensterbank, M. Malacria, E. Lacôte, Angew. Chem. 2010, 122, 9198
14. Angew. Chem. Int. Ed. 2010, 49, 9014
15. S.-H. Ueng, A. Solovyev, X. Yuan, S. J. Geib, L. Fensterbank, E. Lacôte, M. Malacria, M. Newcomb, J. C. Walton, D. P. Curran, J. Am. Chem. Soc. 2009, 131, 11256
16. Q. Chu, M. Makhlouf Brahmi, A. Solovyev, S.-H. Ueng, D. P. Curran, M. Malacria, L. Fensterbank, E. Lacôte, Chem. Eur. J. 2009, 15, 12937
17. S.-H. Ueng, M. Makhlouf Brahmi, E. Derat, L. Fensterbank, E. Lacôte, M. Malacria, D. P. Curran, J. Am. Chem. Soc. 2008, 130, 10082; for the NHC-borane mediated reduction of carbonyl derivatives, see
18. D. M. Lindsay, D. McArthur, Chem. Commun. 2010, 46, 2474.
19. For an exception to this trend, see:, K.-s. Lee, A. R. Zhugralin, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 7253; see also Ref. [3f].
20. S. V. Maifeld, D. Lee, Org. Lett. 2005, 7, 4995
21. G. T. Halvorsen, W. R. Roush, Org. Lett. 2007, 9, 2243
22. R. R. Pidaparthi, M. E. Welker, Tetrahedron Lett. 2007, 48, 7853.
23. M. J. Fuchter, Chem. Eur. J. 2010, 16, 12286
24. M. Tan, Y. Zhang, J. Ying, Adv. Synth. Catal. 2009, 351, 1390; for the extension of this activation to polymerizations, see
25. J. Raynaud, A. Ciolino, A. Baceiredo, M. Destarac, F. Bonete, T. Kato, Y. Gnanou, D. Taton, Angew. Chem. 2008, 120, 5470
26. Angew. Chem. Int. Ed. 2008, 47, 5390
27. J. Raynaud, N. Liu, Y. Gnanou, D. Taton, Macromolecules 2010, 43, 8853; for the activation of a Si-Sn bond, see
28. R. Blanc, L. Commeiras, J.-L. Parrain, Adv. Synth. Catal. 2010, 352, 661; for carbene activation of the Si-H bond in silanes, see
29. G. D. Frey, J. D. Masuda, B. Donnadieu, G. Bertrand, Angew. Chem. 2010, 122, 9634
30. Angew. Chem. Int. Ed. 2010, 49, 9444; for carbene activation of the Si-O bond in siloxanes, see
31. M. Rodriguez, S. Marrot, T. Kato, S. Stérin, E. Fleury, A. Baceiredo, J. Organomet. Chem. 2007, 692, 705.
32. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584
33. Angew. Chem. Int. Ed. 2008, 47, 1560
34. S. N. Tandura, M. G. Voronkov, N. V. Alekseev, Top. Curr. Chem. 1986, 131, 99
35. C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371
36. M. S. Gordon, M. T. Carroll, L. P. Davis, L. W. Burggraf, J. Phys. Chem. 1990, 94, 8125; for an example of imine activation, see
37. A. V. Malkov, S. Stoncius, K. Vrankova, M. Arndt, P. Kocovsky, Chem. Eur. J. 2008, 14, 8082.
38. For silyliums that can complex olefins, see
39. Y. Zhang, F. Lay, P. Garcia-Garcia, B. List, E. Y.-X. Chen, Chem. Eur. J. 2010, 16, 10462
40. T. Müller, C. Bauch, M. Ostermeir, M. Bolte, N. Auner, J. Am. Chem. Soc. 2003, 125, 2158.
41. For tBuOK catalyzed silylations, see:, A. Weickgenannt, A. M. Oestreich, Chem. Asian J. 2009, 4, 406.
42. S. Würtz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523.
43. V. Lavallo, Y. Canac, C. Prasang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851
44. Angew. Chem. Int. Ed. 2005, 44, 5705.
45. D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534.
46. The same silacycles could be obtained through a radical cyclization of the correspoding silane. For this method, see
47. Y. Cai, B. P. Roberts, J. Chem. Soc. Perkin Trans. 1 1998, 467
48. D. L. J. Clive, M. Cantin, J. Chem. Soc. Chem. Commun. 1995, 319
49. A. Martinez-Grau, D. P. Curran, J. Org. Chem. 1995, 60, 8332.
50. A. Abate, E. Brenna, C. Fuganti, F. G. Gatti, T. Giovenzana, L. Malpezzi, S. Serra, J. Org. Chem. 2005, 70, 1281.
51. The saturated silacycles are not stable. See:, A. Studer, H. Steen, Chem. Eur. J. 1999, 5, 759.