Catalytic Hydrophosphination of Alkenylalkyl Ethers

Synlett

Volumn , Issue 14, 2003, Pages 2155-2158

  Kazankova, Marina A ^a   Shulyupin, Mstislav O ^a   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Alkenes; Alkenylalkyl ethers; Hydrophosphination; Nickel; Palladium

Indexed keywords

ALKYL GROUP; ETHER DERIVATIVE; HYDROGEN PEROXIDE; NICKEL; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROPHOSPHINATION; OXIDATION; STEREOCHEMISTRY;

EID: 0344445402     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42092     Document Type: Article

References (45)

1. (a) The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester UK., Vol. 1-4, 1990-1996.
2. (b) Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
3. (c) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization; Togni, A.; Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, 2001, Chap. 5,; and references therein.
4. (d) Beletskaya, I. P.; Kazankova, M. A. Russ. J. Org. Chem. 2002, 38, 1391.
5. (a) Therrien, B.; Koning, A.; Warol, T. R. Organomatallics 1999, 18, 1565.
6. (b) Mitchell, T. N.; Heesche, K. J. J. Organomet. Chem. 1991, 409, 163.
7. (c) Therrien, B.; Ward, T. R. Angew. Chem. Int. Ed. 1999, 38, 405.
8. (d) Malisheva, S. F.; Gusarova, N. K.; Belogorodova, N. A.; Nikitin, M. V.; Gendin, D. V.; Trofimov, B. A. Zh. Obshch. Khim. 1997, 67, 63.
9. (a) Bunlaksananusorn, T.; Knochel, P. Tetrahedron Lett. 2002, 43, 5817.
10. (b) Bookham, J. L.; Smithies, D. M. J. Organomet. Chem. 1999, 577, 305.
11. 2d
12. (b) Dombek, B. D. J. Org. Chem. 1978, 43, 3408.
13. (c) Wolfsberger, W. Chem.-Ztg. 1988, 772, 53.
14. (a) Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223.
15. (b) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701.
16. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis, Vol. 5; Horvath, I. T.; Joo, F., Eds.; Dordrecht: The Netherlands, 1995, 111.
17. (d) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277.
18. (e) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 779, 5039.
19. (f) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49.
20. (g) Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255.
21. (h) Wicht, D. K.; Kourkine, I. V.; Kovacik, I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381.
22. (i) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141.
23. (j) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 79, 950.
24. (a) Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357.
25. (b) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
26. (c) Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824.
27. Shulyupin, M. O.; Kazankova, M. A.; Beletskaya, I. P. Org. Lett. 2002, 4, 761.
28. Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 244, 495.
29. Kazankova, M. A.; Efimova, I. V.; Kochetkov, A. N.; Afanas'ev, V. V.; Beletskaya, I. P.; Dixneuf, P. H. Synlett 2001, 497.
30. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
31. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
32. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
33. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
34. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
35. 2 (X = Cl, Br) react with diphenylphosphine under various conditions to form HX. See for example: (a) Issleib, K.; Wenschuh, E. Z. Anorg. Allg. Chem. 1960, 305, 15. (b) Hayter, R. G. Inorg. Chem. 1963, 2, 932. (c) Hayter, R. G. J. Am. Chem. Soc. 1962, 84, 3046. (d) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313. (e) Weston, C. W.; Bailey, G. W.; Nelson, J. H.; Jonassen, H. B. J. Inorg. Nucl. Chem. 1972, 34, 1752. (f) G iannandrea, R.; Mastrorilli, P.; Nobile, C.-S.; Dilonardo, M. Inorg. Chim. Acta 1996, 249, 237.
36. (a) Backvall, J. E.; Bjorkman, E. E. J. Org. Chem. 1980, 45, 2893.
37. (b) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122.
38. (a) Petrov, K. A.; Chauzov, V. A.; Agafonov, S. V. Zh. Obshch. Khim. 1980, 50, 1510.
39. (b) Mironova, Z. N.; Tzvetkov, E. N.; Nikolaev, A. V.; Kabachnik, M. I.; Dyadin, Yu. A. Zh. Obshch. Khim. 1974, 44, 1217; and references therein,
40. (c) Legin, G. Ya. Zh. Obshch. Chim. 1976, 46, 545.
41. (a) For review see: Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 241.
42. (b) The synthesis of the pheromon of olive fly using 4f, see: Ley, S. V. ; Lygo, B. Tetrahedron Lett. 1984, 24, 113.
43. (a) Artuhin, P. L; Shavinskiy, B. M.; Mityakin, Yu. L.; Mironova, Z. N.; Tzvetkov, E. N.; Nikolaev, A. V.; Kabachnik, M. I. Uzv. AN USSR, Ser. Khim. 1974, 41.
44. (b) Nikolaev, A. V.; Durasov, V. B.; Mironova, Z. N. Dokladi AN USSR 1969, 186, 603.
45. 3): δ = 30.0. Anal. Calcd: C, 71.52; H, 7.61. Found: C, 71.35; H, 7.45.