Silver-catalyzed silacyclopropenation of 1-heteroatom-substituted alkynes and subsequent rearrangement reactions

Organometallics

Volumn 24, Issue 25, 2005, Pages 6212-6219

  Clark, Timothy B ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; SILACYCLOPROPANE; SULFONES;

CATALYSIS; ORGANOMETALLICS; REACTION KINETICS;

SILVER;

EID: 28944453760     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050501z     Document Type: Article

References (66)

1. Gordon, M. S. J. Am. Chem. Soc. 1980, 102, 7419-7422.
2. Goller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840-5846.
3. Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860-2864.
4. Gordon, M. S.; Boatz, J. A.; Walsh R. J. Phys. Chem. 1989, 93, 1584-1585.
5. Conlin, R. T.; Gaspar, P. P. J. Am. Chem. Soc. 1976, 98, 3715-3716.
6. Seyferth, D.; Annarelli, D. C.; Vick, S. C. J. Am. Chem. Soc. 1976, 98, 6382-6384.
7. Seyferth, D.; Annarelli, D. C.; Vick, S. C. J. Organomet. Chem. 1984, 272, 123-139.
8. Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949-957.
9. Franz, A. K.; Woerpel, K. A. Angew. Chem., Int. Ed. 2000, 39, 4295-4299.
10. Franz, A. K.; Woerpel, K. A. Acc. Chem. Res. 2000, 33, 813-820 and references therein.
11. Seyferth, D.; Duncan, D. P.; Shannon, M. L. Organometallics 1984, 3, 579-583.
12. Seyferth, D.; Vick, S. C.; Shannon, M. L. Organometallics 1984, 3, 1897-1905.
13. Boudjouk, P.; Samaraweera, U.; Sooriyakumaran, R.; Chrusciel, J.; Anderson, K. R. Angew. Chem., Int. Ed. Engl. 1988, 27, 1355-1356.
14. Kroke, E.; Willms, S.; Weidenbruch, M.; Saak, W.; Pohl, S.; Marsmann, H. Tetrahedron Lett. 1996, 37, 3675-3678.
15. Clark, T. B.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9522-9523.
16. For reviews of C-Si bond oxidation, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI: Greenwich, CT, 1996; Vol. 3, pp 1-62.
17. (b) Fleming, I. Chemtracts-Org. Chem. 1996, 9, 1-64.
18. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
19. Palmer, W. S.; Woerpel, K. A. Organometallics 1997, 16, 4824-4827.
20. Ćiraković J.; Driver T. G.; Woerpel, K. A. J. Org. Chem. 2004, 69, 4007-4012.
21. See the Experimental Section for details.
22. The structure of 7 was determined by X-ray crystallography (see the Supporting Information for details).
23. Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9993-10002.
24. Steele, K. P.; Weber, W. P. J. Am. Chem. Soc. 1980, 102, 6095-6097.
25. Steele, K. P.; Weber, W. P. Inorg. Chem. 1981, 20, 1302-1304.
26. Kira, M.; Ishida, S.; Iwamoto, T.; Kabuto, C. J. Am. Chem. Soc. 2002, 124, 3830-3831.
27. Gehrhus, B.; Lappert, M. F. J. Organomet. Chem. 2001, 617-618, 209-223.
28. Averbuj, C.; Kaftanov, J.; Marek, I. Synlett 1999, 1939-1941.
29. Morlender-Vais, N.; Kaftanov, J.; Marek, I. Synthesis 2000, 917-920.
30. Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
31. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207-3210.
32. Kartashov, V. R.; Povelikina, L. N.; Skorobogatova, E. V. J. Org. Chem. USSR 1979, 15, 1829-1832.
33. O'Connor, J. M.; Bunker, K. D.; Rheingold, A. L.; Zakharov, L. J. Am. Chem. Soc. 2005, 127, 4180-4181.
34. The nonstatistical crossover is likely due to the different reaction rates of the two alkynes, and formation of insoluble silver halide salts could explain this discrepancy.
35. Alkynes 12 and 13 were combined under the reaction conditions, in the absence of silacyclopropane 1 and were shown to provide no deuterium scrambling.
36. 34b see: (a) March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992; p 250.
37. (b) Burkhard, R. K.; Sellers, D. E.; DeCou, F.; Lambert, J. L. J. Org. Chem. 1959, 24, 767-769.
38. The structure of 17 was determined by X-ray crystallography (see the Supporting Information for details).
39. The isolated silacyclopropene 3d was also subjected to a catalytic amount of CuI under analogous reaction conditions and was also found to provide rearranged alkyne 18.
40. For examples of analogous metal silylenoids with silver and gold, see: (a) Reference 21.
41. (b) Theil, M.; Jutzi, P.; Neumann, B.; Stammler, A.; Stammler, H.-G. J. Organomet. Chem. 2002, 662, 34-42.
42. For examples of sulfonyl oxygen nucleophilic reactivity, including stable y-sultinium ions, see: (a) Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1983, 105, 1061-1063.
43. (b) Carretero, J. C.; Garcia Ruano, J. L.; Martinez, M. C.; Rodriguez, J. H. Tetrahedron 1987, 43, 4417-4423.
44. (c) Lucchini, V.; Modena, G.; Pasquato, L. J. Chem. Soc., Chem. Commun. 1992, 293-294.
45. (d) Saginova, L. G.; Polyakova, O. V.; Shabarov, Y. S. J. Org. Chem. USSR 1992, 28, 938-942.
46. (e) Leca, D.; Song, K.; Amatore, M.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906-916.
47. For the bond dissociation enthalpies of S=N, S=O, Si-N, and Si-O, see: (a) Parsons, S.; Passmore, J. Inorg. Chem. 1992, 31, 526-528.
48. (b) Roux, M. V.; Temprado, M.; Jimenez, P.; Davalos, J. Z.; Notario, R.; Guzman-Mejia, R.; Juaristi, E. J. Org. Chem. 2003, 68, 1762-1770.
49. (c) Johnson, E. R.; Clarkin, O. J.; DiLabio, G. A. J. Phys. Chem. A 2003, 107, 9953-9963.
50. Challis, B. C.; Iley, J. N. J. Chem. Soc., Perkin Trans. 2 1985, 699-703.
51. Kitamura, T.; Kotani, M.; Fujiwara, Y. Synthesis 1998, 1416-1418.
52. Witulski, B.; Buschmann, N.; Bergstraber, U. Tetrahedron 2000, 56, 8473-8480.
53. Ali, H. A.; El Aziz Al Quntar, A.; Goldberg, I.; Srebnik, M. Organometallics 2002, 21, 4533-4539.
54. Inoue, Y.; Fukunaga, T.; Hakushi, T. J. Org. Chem. 1983, 48, 1732-1737.
55. Jiang, M. X.-W.; Rawat, M.; Wulff, W. D. J. Am. Chem. Soc. 2004, 126, 5970-5971.
56. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599-4602.
57. Barluenga, J.; Gonzalez, J. M.; Rodriguez, M. A.; Campos, P. J.; Asensio, G. Synthesis 1987, 661-662.
58. Chen, Z. M.; Trudell, M. L. Synth. Commun. 1994, 24, 3149-3155.
59. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235-5237.
60. Driver, T. G.; Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 6524-6525.
61. Boudjouk, P.; Black, E.; Kumarathason, R. Organometallics 1991, 10, 2095-2096.
62. Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237-5240.
63. Back, T. G.; Collins, S.; Kerr, R. G. J. Org. Chem. 1983, 48, 3077-3084.
64. Kosack, S.; Himbert, G. Chem. Ber. 1987, 120, 71-77.
65. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492.
66. N-Tosyl-N-(4-methylbenzyl)ethynylamine was prepared by a three-step sequence; see the Supporting Information for details.