Taming the silylium ion for low-temperature diels-alder reactions

Angewandte Chemie - International Edition

Volumn 48, Issue 48, 2009, Pages 9077-9079

  Klare, Hendrik F T ^a   Bergander, Klaus ^a   Oestreich, Martin ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Cycloaddition; Homogeneous catalysis; Lewis acids; Silicon; Silylium ions

Indexed keywords

DIELS-ALDER REACTION; ELECTRON-RICH; HOMOGENEOUS CATALYSIS; LEWIS ACID; LEWIS ACIDIC; LEWIS ACIDS; LOW TEMPERATURES; SILICON-BASED; SILYLIUM IONS;

ACIDS; CATALYSIS; CHEMICAL STABILITY; IONS; REACTION RATES; TRANSITION METALS;

SILANES;

EID: 70449601759     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904520     Document Type: Article

References (47)

1. a) J. B. Lambert, Y. Zhao, S. M. Zhang, J. Phys. Org. Chem. 2001, 14, 370 - 379;
2. b) C. A. Reed, Acc. Chem. Res. 1998, 31, 325 - 332;
3. (c) J. B. Lambert, L. Kania, S. Zhang, Chem. Rev. 1995, 95, 1191-1201.
4. For a Highlight, see: J. Belzner, Angew. Chem. 1997, 109, 1331-1334;
5. Angew. Chem. Int. Ed. Engl. 1997, 36, 1277-1280.
6. a) J. B. Lambert, S. Zhang, C. L. Stern, J. C. Huffman, Science 1993, 260, 1917 - 1918;
7. b) J. B. Lambert, S. Zhang, S. M. Ciro, Organometallics 1994, 13, 2430-2443;
8. c) an insightful series of comments on those papers: G. A. Olah, G. Rasul, X.-y. Li, H. A. Buchholz, G. Sandford,G. K. S. Prakash, Science 1994, 263, 983-984;
9. J. B. Lambert, S. Zhang, Science 1994, 263, 984 - 985;
10. C. A. Reed, Z. Xie, Science 1994, 263, 985-986.
11. a) J. B. Lambert, Y. Zhao, Angew. Chem. 1997, 109, 389-391;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 400-401;
13. b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, B. Kuhlmann, J. Am. Chem. Soc. 1999, 121, 5001-5008.
14. S. Duttwyler, Q.-Q. Do, A. Linden, K. K. Baldridge, J. S. Siegel, Angew. Chem. 2008, 120, 1743-1746;
15. Angew. Chem. Int. Ed. 2008, 47, 1719-1722.
16. a) C. A. Reed, Z. Xie, R. Bau, A. Benesi, Science 1993, 262, 402-404;
17. b) Z. Xie, J. Manning, R. W. Reed, R. Mathur, P. D. W. Boyd, A. Benesi, C. A. Reed, J. Am. Chem. Soc. 1996, 118, 2922-2928.
18. a) I. Krossing, I. Raabe, Angew. Chem. 2004, 116, 2116 - 2142;
19. Angew. Chem. Int. Ed. 2004, 43, 2066 - 2090;
20. b) S. H. Strauss, Chem. Rev. 1993, 93, 927-942.
21. K.-C. Kim, C. A. Reed, D.W. Elliott, L. J. Mueller, F. Tham, L. Lin, J. B. Lambert, Science 2002, 297, 825-827.
22. a) V. J. Scott, R. CA elenligil-CA etin, O. V. Ozerov, J. Am. Chem. Soc. 2005, 127, 2852 - 2853;
23. b) C. Douvris, O. V. Ozerov, Science 2008, 321, 1188-1190.
24. R. Panisch, M. Bolte, T. Müller, J. Am. Chem. Soc. 2006, 128, 9676-9682.
25. Highlight: G. Meier, T. Braun, Angew. Chem. 2009, 121, 1575-1577;
26. Angew. Chem. Int. Ed. 2009, 48, 1546-1548.
27. K. Hara, R. Akiyama, M. Sawamura, Org. Lett. 2005, 7, 5621-5623.
28. A. D. Dilman, S. L. Ioffe, Chem. Rev. 2003, 103, 733-772.
29. a) M. Johannsen, K. A. Jørgensen, G. Helmchen, J. Am. Chem. Soc. 1998, 120, 7637 - 7638;
30. b) clarification of that work: G. A. Olah, G. Rasul, G. K. S. Prakash, J. Am. Chem. Soc. 1999, 121, 9615-9617.
31. For neutral (chiral) silicon-based Lewis acids in Diels-Alder chemistry, see: a) B. Mathieu, L. Ghosez, Tetrahedron Lett. 1997, 38, 5497 - 5500;
32. b) B. Mathieu, L. de Fays, L. Ghosez, Tetrahedron Lett. 2000, 41, 9561-9564;
33. (c)B. Mathieu, L. Ghosez, Tetrahedron 2002, 58, 8219-8226.
34. For a chiral, strained silicon Lewis acid in Diels-Alder reactions, see: K. Kubota, C. L. Hamblett, X. Wang, J. L. Leighton, Tetrahedron 2006, 62, 11397-11401.
35. a) J. Y. Corey, D. Gust, K. Mislow, J. Organomet. Chem. 1975, 101, C7 - C8;
36. b) reconsideration of that work: J. B. Lambert, H.-n. Sun, J. Am. Chem. Soc. 1976, 98, 5611 - 5615;
37. (c) T. J. Barton, A. K. Hovland, C. R. Tully, J. Am. Chem. Soc. 1976, 98, 5695-5696.
38. S. C. Bourke, M. J. MacLachlan, A. J. Lough, I. Manners, Chem. Eur. J. 2005, 11, 1989-2000.
39. This statement is based on the observed chemical stability of 2 in CD2Cl2 and our difficulties to spectroscopically characterize less hindered systems.
40. J. Y. Corey, J. Am. Chem. Soc. 1975, 97, 3237-3238.
41. M. Kira, T. Hino, H. Sakurai, J. Am. Chem. Soc. 1992, 114, 6697-6700.
42. F. Frinquelli, A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, Wiley, Chichester, 2002.
43. For remarkable approaches to facilitate demanding Diels-Alder reactions, see: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481 - 1483;
44. b) K. A. Ahrendt, C. J. Borths, D.W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
45. (c) E. J. Corey, T. Shibata, T. W. Lee, J. Am. Chem. Soc. 2002, 124, 3808 - 3809;
46. W. Liu, F. You, C. J. Mocella, W. D. Harman, J. Am. Chem. Soc. 2006, 128, 1426-1427.
47. 3, see: G. Sarakinos, E. J. Corey, Org. Lett. 1999, 1, 1741-1744.