Transition metal-catalysed addition reactions of H–heteroatom and inter-heteroatom bonds to carbon–carbon unsaturated linkages via oxidative additions

Abstract

Oxidative addition of inter-heteroatom bonds comprising B, Si, Ge, Sn, P, S, Se and Te with late transition metal complexes readily takes place at room temperature and triggers a variety of catalytic additions of the bonds to carbon–carbon unsaturated linkages. The new catalytic reactions are regio- and stereo-selective and provide high yield syntheses of synthetically versatile heteroatom compounds.

References

1. For example: M. Beller, Angew. Chem., Int. Ed. Engl., 1995, 34, 1316; A. S. Guram, R. A. Rennels and S. L. Buchwald, Angew. Chem., Int. Ed. Engl., 1995, 34, 1348; J. P. Wolfe, S. Wagaw and S. L. Buchwald, J. Am. Chem. Soc., 1996, 118, 7215; R. A. Widenhoefer and S. L. Buchwald, Organometallics, 1996, 15, 2755; R. A. Singer, J. P. Sadighi and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 213; G. Mann, J. F. Hartwig, M. S. Driver and C. Fernandez-Rivas, J. Am. Chem. Soc., 1998, 120, 827; J. Louie, F. Paul and J. F. Hartwig, Organometallics, 1996, 15, 2794; M. S. Driver and J. F. Hartwig, J. Am. Chem. Soc., 1996, 118, 7217; J. F. Hartwig, Synlett., 1997, 329.
2. Comprehensive Handbook on Hydrosilylation; ed. B. Marciniec, Pergamon, Oxford, UK, 1992; K. A. Horn, Chem. Rev., 1995, 95, 1350; H. K. Sharma and K. H. Pannell, Chem. Rev., 1995, 95, 1351; S. Murai and N. Chatani, J. Synth. Org. Chem., Jpn., 1993, 51, 421; C. A. Recatto, Aldrichim. Acta, 1995, 28, 85; R. J. P. Corriu and J. J. E. Moreau, J. Organomet. Chem., 1972, 40, 73; Y. Ichinose, H. Oda, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1987, 60, 3468; K. Kikukawa, H. Umekawa, F. Wada and T. Matsuda, Chem. Lett., 1988, 881; H. X. Zhang, F. Guibe and G. Balavoine, J. Org. Chem., 1990, 55, 1857; T. N. Mitchell, A. Amamria, H. Killing and D. Rutschow, J. Organomet. Chem., 1983, 241, C45; H. Killing and T. N. Mitchel, Organometallics, 1984, 3, 1318; E. Piers and R. T. Skerlj, J. Chem. Soc., Chem. Commun., 1986, 626; T. N. Mitchell and U. Schneider, J. Organomet. Chem., 1991, 407, 319 and references cited therein.
3. K. Burgess and M. J. Ohlmeyer, Chem. Rev., 1991, 91, 1179; I. Beletskaya and A. Pelter, Tetrahedron, 1997, 53, 4957.
4. T. Ishiyama, N. Matsuda, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 11018; T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki and N. Miyaura, Organometallics, 1996, 15, 713.
5. C. N. Iverson and M. R. I. Smith, J. Am. Chem. Soc., 1995, 117, 4403; C. N. Iverson and M. R. I. Smith, Organometallics, 1996, 15, 5155.
6. G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg and N. C. Norman, Organometallics, 1996, 15, 5137.
7. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1996, 2073.
8. R. T. Baker, P. Nguyen, T. B. Marder and S. A. Westcott, Angew. Chem., Int. Ed. Engl., 1995, 34, 1336.
9. T. Ishiyama, M. Yamamoto and N. Miyaura, Chem. Commun., 1997, 689; C. N. Iverson and M. R. Smith III, Organometallics, 1997, 16, 2757.
10. S.-y. Onozawa, Y. Hatanaka, T. Sakakura, S. Shimada and M. Tanaka, Organometallics, 1996, 15, 5450.
11. S.-y. Onozawa, Y. Hatanaka, N. Choi and M. Tanaka, Organometallics, 1997, 16, 5389.
12. S.-y. Onozawa, Y. Hatanaka and M. Tanaka, Tetrahedron Lett, in the press.
13. T. Hayashi, A. M. Kawamoto, T.-a. Kobayashi and M. Tanaka, J. Chem. Soc., Chem. Commun., 1990, 563; H. Yamashita, M. Catellani and M. Tanaka, Chem. Lett., 1991, 241; H. Yamashita and M. Tanaka, Chem. Lett., 1992, 1547; T. Hayashi, H. Yamashita, T. Sakakura, Y. Uchimaru and M. Tanaka, Chem. Lett., 1991, 245; H. Yamashita, N. P. Reddy and M. Tanaka, Macromolecules, 1993, 26, 2143.
14. S.-y. Onozawa, Y. Hatanaka and M. Tanaka, Chem. Commun., 1997, 1229.
15. Y. Ito, M. Suginome and M. Murakami, J. Org. Chem., 1991, 56, 1948; M. Suginome, H. Oike, S.-S. Park and Y. Ito, Bull. Chem. Soc. Jpn., 1996, 69, 289.
16. M. Suginome, H. Nakamura and Y. Ito, Chem. Commun., 1996, 2777.
17. M. Suginome, H. Nakamura and Y. Ito, Angew. Chem., Int. Ed. Engl., 1997, 36, 2516.
18. Similar 1,1-adducts were formed in dehydrogenative double silylation of 1-alkenes with 1,2-bis(dim ethylsilyl)benzene. See M. Tanaka, Y. Uchimaru and H.-J. Lautenschlager, J. Organomet. Chem., 1992, 428, 1.
19. T. Ishiyama, K.-i. Nishijima, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 7219.
20. M. B. Gasc, A. Lattes and J. J. Perie, Tetrahedron, 1983, 39, 703; L. S. Hegedus, Angew. Chem., Int. Ed. Engl., 1988, 27, 1113; J.-J. Brunet, D. Neibecker and F. Niedercorn, J. Mol. Catal., 1989, 49, 235.
21. Hydroaminations catalysed by organolanthanides have been developed. However, they will not be discussed here since they proceed viaa different mechanism from that shown in Scheme 1. See P. J. Walsh, A. M. Baranger and R. G. Bergman, J. Am. Chem. Soc., 1992, 114, 1708; M. A. Giardello, V. P. Conticello, L. Brard, M. R. Gagne and T. J. Marks, J. Am. Chem. Soc., 1994, 116, 10241; Y. Li and T. J. Marks, Organometallics, 1996, 15, 3770; Y. Li and T. J. Marks, J. Am. Chem. Soc., 1996, 118, 9295; A. Haskel, T. Straub and M. S. Eisen, Organometallics, 1996, 15, 3773.
22. A. L. Casalnuovo, J. C. Calabrese and D. Milstein, J. Am. Chem. Soc., 1988, 110, 6738.
23. J.-J. Brunet, G. Commenges, D. Neibecker and K. Philippot, J. Organomet. Chem., 1994, 469, 221.
24. R. Dorta, P. Egli, F. Zürcher and A. Togni, J. Am. Chem. Soc., 1997, 119, 10857.
25. M. Al-Masum, M. Meguro and Y. Yamamoto, Tetrahedron Lett., 1997, 38, 6071.
26. P. G. Pringle and M. B. Smith, J. Chem. Soc., Chem. Commun., 1990, 1701.
27. D. K. Wicht, I. V. Kourkine, B. M. Lew, J. M. Nthenge and D. S. Glueck, J. Am. Chem. Soc., 1997, 119, 5039.
28. L.-B. Han and M. Tanaka, J. Am. Chem. Soc., 1996, 118, 1571.
29. L.-B. Han and M. Tanaka, unpublished results.
30. L.-B. Han, N. Choi and M. Tanaka, Organometallics, 1996, 15, 3259.
31. W. B. Beaulieu, T. B. Rauchfuss and D. M. Roundhill, Inorg. Chem., 1975, 14, 1732; P. W. N. M. van Leeuwen, C. F. Roobeek, R. L. Wife and J. H. G. Frijns, J. Chem. Soc., Chem. Commun., 1986, 31.
32. L.-B. Han, R. Hua and M. Tanaka, Angew. Chem., Int. Ed., 1998, 37, 94.
33. L.-B. Han, N. Choi and M. Tanaka, J. Am. Chem. Soc., 1996, 118, 7000.
34. A. Ogawa and N. Sonoda, J. Synth. Org. Chem., Jpn., 1996, 54, 894; A. Ogawa and N. Sonoda, J. Synth. Org. Chem., Jpn., 1993, 51, 815.
35. H. Kuniyasu, A. Ogawa, K.-I. Sato, I. Ryu, N. Kambe and N. Sonoda, J. Am. Chem. Soc., 1992, 114, 5902; H. Kuniyasu, A. Ogawa, K.-I. Sato, I. Ryu and N. Sonoda, Tetrahedron Lett., 1993, 34, 2491.
36. A. Ogawa, J.-i. Kawakami, N. Sonoda and T. Hirao, J. Org. Chem., 1996, 61, 4161.
37. J.-E. Bäckvall and A. Ericsson, J. Org. Chem., 1994, 59, 5850.
38. A. Ogawa, M. Takeba, J.-i. Kawakami, I. Ryu, N. Kambe and N. Sonoda, J. Am. Chem. Soc., 1995, 117, 7564.
39. H. Kuniyasu, A. Ogawa, S.-I. Miyazaki, I. Ryu, N. Kambe and N. Sonoda, J. Am. Chem. Soc., 1991, 113, 9796; Y. Gareau and A. Orellana, Synlett., 1997, 803.
40. A. Ogawa, H. Kuniyasu, N. Sonoda and T. Hirao, J. Org. Chem., 1997, 62, 8361.
41. H. Kuniyasu, K. Sugoh, M. S. Su and H. Kurosawa, J. Am. Chem. Soc., 1997, 119, 4669.
42. For references, see ref. 34, 39 and 41 and literature cited therein.
43. Reviews >R. J. Angelici, Acc. Chem. Res., 1988, 21, 387; R. J. Angelici, Coord. Chem. Rev., 1990, 105, 61; R. A. Sánchez-Delgado, J. Mol. Catal., 1994, 86, 287 For other examples, see K. Matsubara, R. Okamura, M. Tanaka and H. Suzuki, J. Am. Chem. Soc., 1998, 120, 1108 and references cited therein.
44. L.-B. Han, N. Choi and M. Tanaka, J. Am. Chem. Soc., 1997, 119, 1795.
45. L.-B. Han, S. Shimada and M. Tanaka, J. Am. Chem. Soc., 1997, 119, 8133.
46. L.-B. Han and M. Tanaka, Chem. Commun., 1998, 47; T. Stüdemann, V. Gupta, L. Engman and P. Knochel, Tetrahedron Lett., 1997, 38, 1005.
47. L.-B. Han and M. Tanaka, J. Am. Chem. Soc., 1998, 120, 8249.