Palladium-catalyzed hydrophosphorylation of alkynes via oxidative addition of HP(O)(OR)2

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1571-1572

  Han, Li Biao ^a   Tanaka, Masato ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030001647     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953690t     Document Type: Article

References (33)

1. (a) Chaloner, P. A. Handbook of Coordination Catalysis in Organic Chemistry; Butterworth: London, 1986; Chapter 4.
2. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Hill Valley, CA, 1987.
3. (c) Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, pp 667-792.
4. (d) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; John Wiley & Sons: New York, 1992; pp 25-50.
5. Comprehensive Handbook on Hydrosilylation; Marciniec, B., Ed.; Pergamon Press: Oxford, U.K., 1992.
6. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
7. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
8. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
9. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
10. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
11. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
12. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
13. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1350. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. (d) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754. (e) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157. (g) Shimada, S.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8289. (h) Yamashita, H.; Tanaka, M.; Hond, K. J. Am. Chem. Soc. 1995, 117, 8873.
14. For radical and acid- or base-catalyzed addition of H-P, see: (a) Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972. (b) Goldwhite, H. Introduction to Phosphorus Chemistry; Cambridge University Press: Cambridge, 1981.
15. For radical and acid- or base-catalyzed addition of H-P, see: (a) Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972. (b) Goldwhite, H. Introduction to Phosphorus Chemistry; Cambridge University Press: Cambridge, 1981.
16. 2(OH), the former being thermodynamically more favored under ambient conditions. They coordinate, like tertiary phosphines, to transition metals (Pd. Pt. Ir, Rh, etc.) to form complexes which have been used as catalysts in organic reactions: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785. (b) Roundhill, D. M.; Sperline, R. P; Beaulieu, W. B. Coord. Chem. Rev. 1978, 26, 263. (c) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223.
17. 2(OH), the former being thermodynamically more favored under ambient conditions. They coordinate, like tertiary phosphines, to transition metals (Pd. Pt. Ir, Rh, etc.) to form complexes which have been used as catalysts in organic reactions: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785. (b) Roundhill, D. M.; Sperline, R. P; Beaulieu, W. B. Coord. Chem. Rev. 1978, 26, 263. (c) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223.
18. 2(OH), the former being thermodynamically more favored under ambient conditions. They coordinate, like tertiary phosphines, to transition metals (Pd. Pt. Ir, Rh, etc.) to form complexes which have been used as catalysts in organic reactions: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785. (b) Roundhill, D. M.; Sperline, R. P; Beaulieu, W. B. Coord. Chem. Rev. 1978, 26, 263. (c) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223.
19. For a recent review, see: Minami, T.; Motoyoshiya. J. Synthesis 1992, 333.
20. (a) Engel, R. Chem. Rev. 1977, 77, 349.
21. (b) Harnden, M. R.; Parkin, A.; Parrart, M. J.; Perkins, R. M. J. Med. Chem. 1993, 36, 1345.
22. (c) Breaker, R. R.; Gough, G. R.; Gilham, P. T. Biochemistry 1993, 32, 9125.
23. Some of these Pd(II) complexes appeared to react with the phosphonate since a distinct color change of the solution was observed upon mixing these two components.
24. 2-carbon to phosphorus bond-forming reactions are rare: (a) Hirao, T.; Masunaga, T.; Yamada, N.; Oshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (b) Xu, Y., Li, Z.; Xia, J.; Guo, H.; Huang, Y. Synthesis 1983, 377. (c) Holt, D. A., Erb, J. M. Tetrahedron Lett. 1989, 30, 5393.
25. 2-carbon to phosphorus bond-forming reactions are rare: (a) Hirao, T.; Masunaga, T.; Yamada, N.; Oshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (b) Xu, Y., Li, Z.; Xia, J.; Guo, H.; Huang, Y. Synthesis 1983, 377. (c) Holt, D. A., Erb, J. M. Tetrahedron Lett. 1989, 30, 5393.
26. 2-carbon to phosphorus bond-forming reactions are rare: (a) Hirao, T.; Masunaga, T.; Yamada, N.; Oshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. (b) Xu, Y., Li, Z.; Xia, J.; Guo, H.; Huang, Y. Synthesis 1983, 377. (c) Holt, D. A., Erb, J. M. Tetrahedron Lett. 1989, 30, 5393.
27. 2 also exhibited similar reactivities toward HP(O)-(OR)2, but required somewhat severer conditions. Full details will be separately reported.
28. For Rh and Ir complexes, see: (a) Duncan, J. A. S.; Hedden, D.; Roundhill, D. M.; Stephenson, T. A.; Walkinshaw, M. D. Angew. Chem., Int. Ed. Engl. 1982, 21, 452. (b) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223. (c) Varshney, A.; Gray, G. M. J. Organomet. Chem. 1990, 391, 415. See also: Nakazawa, H.; Matsuoka, Y., Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385.
29. For Rh and Ir complexes, see: (a) Duncan, J. A. S.; Hedden, D.; Roundhill, D. M.; Stephenson, T. A.; Walkinshaw, M. D. Angew. Chem., Int. Ed. Engl. 1982, 21, 452. (b) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223. (c) Varshney, A.; Gray, G. M. J. Organomet. Chem. 1990, 391, 415. See also: Nakazawa, H.; Matsuoka, Y., Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385.
30. For Rh and Ir complexes, see: (a) Duncan, J. A. S.; Hedden, D.; Roundhill, D. M.; Stephenson, T. A.; Walkinshaw, M. D. Angew. Chem., Int. Ed. Engl. 1982, 21, 452. (b) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223. (c) Varshney, A.; Gray, G. M. J. Organomet. Chem. 1990, 391, 415. See also: Nakazawa, H.; Matsuoka, Y., Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385.
31. For Rh and Ir complexes, see: (a) Duncan, J. A. S.; Hedden, D.; Roundhill, D. M.; Stephenson, T. A.; Walkinshaw, M. D. Angew. Chem., Int. Ed. Engl. 1982, 21, 452. (b) Bennett, M. A.; Mitchell, T. R. B. J. Organomet. Chem. 1985, 295, 223. (c) Varshney, A.; Gray, G. M. J. Organomet. Chem. 1990, 391, 415. See also: Nakazawa, H.; Matsuoka, Y., Nakagawa, I.; Miyoshi, K. Organometallics 1992, 11, 1385.
32. 3, and u foregoing couplings develop to become evident.
33. 2 moieties bonding to Pt disappeared, indicative of the reversibility of the oxidative addition reaction.