Oxidative addition of HP(O)Ph2 to platinum(O) and palladium(O) complexes and palladium-catalyzed regio-and stereoselective hydrophosphinylation of alkynes

Organometallics

Volumn 15, Issue 15, 1996, Pages 3259-3261

  Han, Li Biao ^a   Choi, Nami ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000617783     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960328u     Document Type: Article

References (57)

1. (a) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
2. (b) Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49-50, 263.
3. (a) Horner, L.; Lindel, H. Phosphorus Sulfur Relat. Elem. 1984, 20, 161.
4. (b) Pietrusiewicz, K. M.; Wisniewski, W.; Zablocka, M. Tetrahedron 1989, 45, 337.
5. (a) Collins, D. J.; Rowley, L. E.; Swan, J. M. Aust. J. Chem. 1974, 27, 841.
6. (b) Polikarpov, Y. M.; Sacherbalkov, B. K.; Medved, T. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 2114.
7. (c) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991.
8. (d) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 417, 173.
9. (e) Cavalla, D.; Warren, S. Tetrahedron Lett. 1982, 23, 4505.
10. (a) Kabachnik, M. I.; Medved, T. Y.; Polikarpov, Y. M.; Yudina, K. S. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 1584.
11. (b) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 413, 55.
12. (a) Berlan, J.; Battioni, J.-P.; Koosha, K. Tetrahedron Lett. 1976, 3351.
13. (b) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 937
14. (a) Keck, G. E.; Byers, J. H.; Tafesh, A. M. J. Org. Chem. 1988, 53, 1127.
15. (b) Brandi, A.; Cicchi, S.; Goti, A. Tetrahedron Lett. 1991, 32, 3265.
16. (a) Haynes, R. K.; Vonwiller, S. C.; Hambley, T. W. J. Org. Chem. 1989, 54, 5162.
17. (b) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785.
18. (c) Birse, E. F.; Ironside, M. D.; Murray, A. W. Tetrahedron Lett. 1995, 36, 6309.
19. (d) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825.
20. (e) Yamashita, K.; Oshikawa, T.; Imoto, H. Jpn. Kokai Tokkyo Koho JP 62 207281, 1987; Chem. Abstr. 1988, 108, 167691m.
21. (f) Yamashita, K.; Imoto, H.; Tamada, Y.; Oshikawa, T. Jpn. Kokai Tokkyo Koho JP 01 45390, 1989; Chem. Abstr. 1989, 111, 115592x.
22. (a) Welch, F. J. U.S. 3312674, 1967; Chem. Abstr. 1967, 67, 11967e.
23. (b) Rabinowitz, R. Ger. 1241995, 1967; Chem. Abstr. 1967, 67, 44417d.
24. (c) Cooper, R. S. U.S. 3340477, 1967; Chem. Abstr. 1968, 68, 3515m.
25. (d) Juelke, C. V.; Trapasso, L. E. U.S. 3813454, 1974; Chem. Abstr. 1975, 83, 81053h.
26. (e) Stackman, R. W. Ind. Eng. Chem. Prod. Res. Develop. 1982, 21, 328.
27. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
28. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
29. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
30. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
31. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
32. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
33. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
34. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
35. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
36. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
37. Via reactions of alkenyl species: (a) Babinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623. (b) Welch, F. J.; Paxton, H. J. Polym. Sci., Part A 1965, 3, 3439. (c) Bergmann, E. D.; Dror, M. Isr. J. Chem. 1966, 3, 239. (d) Xu, Y.; Xia, J.; Guo, H. Synthesis 1986, 691. Via elimination and related reactions: (e) Postle, S. R.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 2084. (f) Santelli-Rouvier, C. Synthesis 1988, 64. (g) Yamashita, M.; Tamada, Y.; Iida, A.; Oshikawa, T. Synthesis 1990, 420. (h) Yamashita, M.; Tsunekawa, K.; Sugiura, M.; Oshikawa, T. Synthesis 1985, 65. (i) Imoto, H.; Yamashita, M. Synthesis 1988, 323. Via other reactions: (j) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848. (k) Huang, X.; Zhang, C.; Lu, X. Synthesis 1995, 769.
38. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
39. Secondary phosphine oxides exist in two tautomeric isomers, P(=O)H and P-OH, the former being dominant in the equilibrium. See: (a) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1963, 28, 531. (b) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1964, 29, 1013. (c) Hamilton, L. A.; Landis, P. S. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley: New York, 1972; Vol. 4, Chapter 11.
40. Secondary phosphine oxides exist in two tautomeric isomers, P(=O)H and P-OH, the former being dominant in the equilibrium. See: (a) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1963, 28, 531. (b) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1964, 29, 1013. (c) Hamilton, L. A.; Landis, P. S. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley: New York, 1972; Vol. 4, Chapter 11.
41. Secondary phosphine oxides exist in two tautomeric isomers, P(=O)H and P-OH, the former being dominant in the equilibrium. See: (a) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1963, 28, 531. (b) Bailey, W. J.; Fox, R. B. J. Org. Chem. 1964, 29, 1013. (c) Hamilton, L. A.; Landis, P. S. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley: New York, 1972; Vol. 4, Chapter 11.
42. 2P(O)H to Pt complexes has been confirmed by an NMR study: (a) Beaulieu, W. B.; Rauchfuss, T. B.; Roundhill, D. M. Inorg. Chem. 1975, 14, 1732. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F.; Wife, R. L.; Frijns, J. H. G. J. Chem. Soc., Chem. Commun. 1986, 31.
43. 2P(O)H to Pt complexes has been confirmed by an NMR study: (a) Beaulieu, W. B.; Rauchfuss, T. B.; Roundhill, D. M. Inorg. Chem. 1975, 14, 1732. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F.; Wife, R. L.; Frijns, J. H. G. J. Chem. Soc., Chem. Commun. 1986, 31.
44. Roundhill, D. M.; Sperline, R. P.; Beaulieu, W. B. Coord. Chem. Rev. 1978, 26, 263.
45. Radical or base-catalyzed addition of RaP(O)H to alkynes are known. For example, see: (a) Solovetskaya, L. A.; Sergeev, N. M.; Magdeeva, R. K.; Nifant'ev, E. E. Zh. Obshch. Khim. 1985, 55, 1201. (b) Nifant'ev, E. E.; Solovetskaya, L. A.; Magdeeva, R. K. Zh. Obshch. Khim. 1985, 55, 2263. (c) Antoshin, A. E.; Khartonov, A. V.; Tsvetkov, E. N. Zh. Obshch. Khim. 1992, 62, 1264.
46. Radical or base-catalyzed addition of RaP(O)H to alkynes are known. For example, see: (a) Solovetskaya, L. A.; Sergeev, N. M.; Magdeeva, R. K.; Nifant'ev, E. E. Zh. Obshch. Khim. 1985, 55, 1201. (b) Nifant'ev, E. E.; Solovetskaya, L. A.; Magdeeva, R. K. Zh. Obshch. Khim. 1985, 55, 2263. (c) Antoshin, A. E.; Khartonov, A. V.; Tsvetkov, E. N. Zh. Obshch. Khim. 1992, 62, 1264.
47. Radical or base-catalyzed addition of RaP(O)H to alkynes are known. For example, see: (a) Solovetskaya, L. A.; Sergeev, N. M.; Magdeeva, R. K.; Nifant'ev, E. E. Zh. Obshch. Khim. 1985, 55, 1201. (b) Nifant'ev, E. E.; Solovetskaya, L. A.; Magdeeva, R. K. Zh. Obshch. Khim. 1985, 55, 2263. (c) Antoshin, A. E.; Khartonov, A. V.; Tsvetkov, E. N. Zh. Obshch. Khim. 1992, 62, 1264.
48. 31P NMR, suggesting the reversibility of the reaction of eq 1.
49. P-P(O) = 305.9 Hz).
50. Carty, A. J.; Jacobson, S. E.; Simpson, R. T.; Taylor, N. J. J. Am. Chem. Soc. 1975, 97, 7254 and referencies cited therein.
51. Corbridge, D. E. C. Top. Phosphorus Chem. 1966, 3, 57.
52. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
53. 6, on standing at room temperature, remained unchanged. Diphenylphosphine oxide was extruded as the decomposition progressed.
54. 6 was heated at 70 °C for 5 h.
55. 4 as catalyst, neither the use of an excess of Ph2P(O)H (2 equiv) nor the use of other solvents such as THF and MeCN suppressed the formation of the byproducts.
56. 3 as eluent to yield a mixture of adducts 2 as a white solid (63 mg, 0.201 mmol, 2a/2b = 96/4). These two regioisomers (2a,b) were separated by preparative TLC (silica gel, hexane/EtOAc = 2/3).
57. 1H NMR confirmed that the regioaelectivity was nearly constant throughout the reaction. Accordingly, the unusual selectivity is not due to an isomerization of an initially formed isomer.