Salt-free preparation of trimethylsilyl ethers by B(C6F 5)3-catalyzed transfer silylation by using a Me 3SiH surrogate

European Journal of Organic Chemistry

Volumn 2014, Issue 10, 2014, Pages 2077-2083

  Simonneau, Antoine ^a   Friebel, Jonas ^a   Oestreich, Martin ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Dehydrogenative coupling; Lewis acids; Si H activation; Silane transfer; Silicon

Indexed keywords

EID: 84897109526     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301840     Document Type: Article

References (54)

1. S. Rendler, M. Oestreich, Angew. Chem. 2008, 120, 6086-6089
2. Angew. Chem. Int. Ed. 2008, 47, 5997-6000.
3. D. T. Hog, M. Oestreich, Eur. J. Org. Chem. 2009, 5047-5056.
4. M. Mewald, R. Fröhlich, M. Oestreich, Chem. Eur. J. 2011, 17, 9406-9414.
5. M. Mewald, M. Oestreich, Chem. Eur. J. 2012, 18, 14079-14084.
6. J. Hermeke, M. Mewald, M. Oestreich, J. Am. Chem. Soc. 2013, 135, 17537-17546.
7. A. Simonneau, M. Oestreich, Angew. Chem. 2013, 125, 12121-12124
8. Angew. Chem. Int. Ed. 2013, 52, 11905-11907.
9. A. Simonneau, M. Oestreich, EP 13183727.0.
10. D. J. Parks, J. M. Blackwell, W. E. Piers, J. Org. Chem. 2000, 65, 3090-3098.
11. 3, see
12. T. Robert, M. Oestreich, Angew. Chem. 2013, 125, 5324-5326
13. Angew. Chem. Int. Ed. 2013, 52, 5216-5218.
14. G. Erker, Dalton Trans. 2005, 1883-1890.
15. W. E. Piers, Adv. Organomet. Chem. 2004, 52, 1-76.
16. W. E. Piers, T. Chivers, Chem. Soc. Rev. 1997, 26, 345-354.
17. 3, see:, M. Rubin, T. Schwier, V. Gevorgyan, J. Org. Chem. 2002, 67, 1936-1940.
18. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887-4892.
19. P. G. M. Wuts, T. W. Greene, Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, New York, 2007, p. 165-221.
20. P. J. Kocieńsky, Protecting Groups, 3rd ed., Thieme, Stuttgart, Germany, 2005, p. 188-230.
21. J. Y. Corey in Advances in Silicon Chemistry, vol. 1 (Ed.:, G. Larson), JAI Press, Greenwich, 1991, p. 327-387.
22. C. Lorenz, U. Schubert, Chem. Ber. 1995, 128, 1267-1269; for a mechanistic discussion, see
23. S. Rendler, O. Plefka, B. Karatas, G. Auer, R. Fröhlich, C. Mück-Lichtenfeld, S. Grimme, M. Oestreich, Chem. Eur. J. 2008, 14, 11512-11528; for selected recent examples, see
24. H. Ito, T. Saito, T. Miyahara, C. Zhong, M. Sawamura, Organometallics 2009, 28, 4829-4840.
25. A. Weickgenannt, M. Mewald, T. W. T. Muesmann, M. Oestreich, Angew. Chem. 2010, 122, 2269-2272
26. Angew. Chem. Int. Ed. 2010, 49, 2223-2226.
27. D. Mukherjee, R. R. Thompson, A. Ellern, A. D. Sadow, ACS Catal. 2011, 1, 698-702.
28. E. Lukevics, M. Dzintara, J. Organomet. Chem. 1985, 295, 265-315.
29. A. Weickgenannt, M. Oestreich, Chem. Asian J. 2009, 4, 406-410.
30. A. Grajewska, M. Oestreich, Synlett 2010, 2482-2484.
31. D. Gao, C. Cui, Chem. Eur. J. 2013, 19, 11143-11147.
32. B. B. Liau, B. C. Milgram, M. D. Shair, J. Am. Chem. Soc. 2012, 134, 16765-16772.
33. L. Jørgensen, S. J. McKerrall, C. A. Kuttruff, F. Ungeheuer, J. Felding, P. S. Baran, Science 2013, 341, 878-882.
34. A. E. Pierce, Silylation of Organic Compounds (A Technique for Gas Phase Analysis), Pierce Chemical Co., Rockford, 1968.
35. C. C. Sweeley, R. Bentley, M. Makita, W. W. Wells, J. Am. Chem. Soc. 1963, 85, 2497-2507.
36. C. A. Bruynes, T. K. Jurriens, J. Org. Chem. 1982, 47, 3966-3969.
37. For a seminal example, see:, J. F. Klebe, H. Finkbeiner, D. M. White, J. Am. Chem. Soc. 1966, 88, 3390-3395.
38. T. Morita, Y. Okamoto, H. Sakurai, Tetrahedron Lett. 1980, 21, 835-838; for selected examples with the use of other Brønsted acids, see
39. G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem, S. C. Narang, J. Org. Chem. 1981, 46, 5212-5214.
40. G. A. Olah, A. Husain, B. P. Singh, Synthesis 1983, 892-895; for a related alcohol silylation by employing different electrophiles, see
41. A. Hosomi, H. Sakurai, Chem. Lett. 1981, 85-88.
42. J.-W. Park, H.-J. Chang, C.-H. Jun, Synlett 2006, 771-775.
43. J.-W. Park, C.-H. Jun, Org. Lett. 2007, 9, 4073-4076.
44. C. Bergquist, B. M. Bridgewater, C. J. Harlan, J. R. Norton, R. A. Friesner, G. Parkin, J. Am. Chem. Soc. 2000, 122, 10581-10590.
45. V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919-8922.
46. V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179-6186.
47. 3 was reported:, C. B. Caputo, D. W. Stephan, Organometallics 2012, 31, 27-30.
48. E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70-73.
49. A. Iida, A. Horii, T. Misaki, Y. Tanabe, Synthesis 2005, 2677-2682.
50. B. Wrackmeyer, G. Guldner, S. T. Abu-Orabi, Tetrahedron 1989, 45, 1119-1130.
51. J. S. Yadav, B. V. S. Reddy, A. K. Basak, G. Baishya, A. V. Narsaiah, Synthesis 2006, 3831-3834.
52. H. R. Shaterian, M. Ghashang, Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 194-204.
53. G. Rajagopal, H. Lee, S. S. Kim, Tetrahedron 2009, 65, 4735-4741.
54. S. Kim, M. S. Kwon, J. Park, Tetrahedron Lett. 2010, 51, 4573-4575.