New Approach to Phosphinoalkynes Based on Pd- and Ni-Catalyzed Cross-Coupling of Terminal Alkynes with Chlorophosphanes

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4309-4311

  Beletskaya, Irina P ^a   Afanasiev, Vladimir V ^a   Kazankova, Marina A ^a   Efimova, Irina V ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; NICKEL; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION;

EID: 0345603481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035562c     Document Type: Article

References (42)

1. (a) The Chemistry of Organophosphorus Compounds; Hartley, F. R.; Ed.; Wiley: Chichester, U.K., 1990-1996; Vols. 1-4.
2. (b) Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
3. (c) Muller, E. Methoden der Organischen Chemie (Houben-Weyl); Georg Thieme Verlag: Stuttgart, 1977; Band 5/Teil 2.
4. (a) Taylor, N. J.; Carty, A. J. J. Chem. Soc., Dalton Trans. 1976, 799.
5. (b) Carty, A. J.; Jacobson, S. E.; Taylor, N. J. J. Am. Chem. Soc. 1975, 97, 7254.
6. (c) Carty, A. J.; Johnson D. K.; Jacobson, S. E. J. Am. Chem. Soc. 1979, 101, 1, 5612.
7. (d) Liu, X.; Mok, K. F.; Leung, P.-H. Organometallics 2001, 20, 3918.
8. (a) Liu, X.; Ong, T. K. W.; Selvaratnam, S.; Vittal, J. J.; White A. J. P.; Williams, D. J.; Leung, P.-H. J. Organomet. Chem. 2002, 643-644, 4.
9. (b) Markl, G.; Matthes, D. Angew. Chem., Int. Ed. Engl. 1972, 11, 1019.
10. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
11. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
12. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
13. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
14. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
15. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
16. See for example: (a) Moldes, J.; De la Encarnacion, E.; Ros, J.; Alvarez-Larena, A.; Piniella, J. F. J. Organomet. Chem. 1998, 566, 165. (b) Rosa, P.; Le Floch, P.; Richard, L.; Mathey, F. J. Am. Chem. Soc. 1997, 119, 9417. (c) Jeffery, J. C.; Pereira R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805. (d) Johnson, D. K.; Rukachasirikul, T.; Sun, Y. ; Taylor, N. J.; Carty, A. J. Inorg. Chem. 1993, 32, 5544. (e) Berenguer, J. R. ; Bernechea, M.; Fornies, J.; Gomes, J.; Lalinde, E. Organometallics 2002, 21, 2314. (f) Ara, J.; Falvello, L. R.; Fernandes, S.; Fornies, J.; Lalinde, E.; Martin, A.; Moreno, T. Organometallics 1997, 16, 5923. (g) Lauattani, E.; Suades, J.; Matheim, R. J. Organomet. Chem. 1991, 421, 335.
17. (a) Davidsohn, W. E.; Henry, M. C. Chem. Rev. 1967, 73.
18. (b) Ionin, B. I.; Bogolubov, G. M.; Petrov, A. A. Russ. Chem. Rev. 1967, 36, 587.
19. (c) Charrier, C.; Chodkiewic, Z. W.; Cadiot, P. Bull. Chem. Soc. Fr. 1966, 1002.
20. (d) Carty, A. J.; Hota, N. K.; Ng, T. W.; Patel, H. A.; O'Connor, T. J. Can. J. Chem. 1971, 49, 2706.
21. (e) Bharathi, P.; Periasamy, M. Organometallics 2000, 19, 5511.
22. (a) Beletskaya, I. P.; Kazankova, M. A. Russ. J. Org. Chem. 2002, 38, 1391.
23. (b) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
24. (c) Allen, D. V.; Venkataraman, D. V. J. Org. Chem. 2003, 68, 4590.
25. (d) Gelman, D.; Jang, L.; Buchwald, S. L. Org. Lett. 2003, 3, 2315.
26. Hand Book of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-VCH: New York, 2002.
27. 3 with phenylacetylene: Michailov, G. J.; Trostyanskaya, I. G.; Kazankova, M. A.; Lutsenko, I. F. Zh. Obshch. Chim. 1987, 57, 2636.
28. For oxidative addition of phosphanes and phosphane oxides P-H bond to Pt(0), Pd(0), or Ni(0) centers, see: (a) Jasaka, C. A.; Dorn, H.; Lough, A. N.; Manners, L. Chem. Eur. J. 2003, 9, 271. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (c) Gianandrea, R.; Mastrorilly, R.; Nolill, C. F.; Englert, U. J. Chem. Soc., Dalton Trans. 1997, 1355. (d) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, 2001; Chapter 5 and references therein.
29. For oxidative addition of phosphanes and phosphane oxides P-H bond to Pt(0), Pd(0), or Ni(0) centers, see: (a) Jasaka, C. A.; Dorn, H.; Lough, A. N.; Manners, L. Chem. Eur. J. 2003, 9, 271. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (c) Gianandrea, R.; Mastrorilly, R.; Nolill, C. F.; Englert, U. J. Chem. Soc., Dalton Trans. 1997, 1355. (d) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, 2001; Chapter 5 and references therein.
30. For oxidative addition of phosphanes and phosphane oxides P-H bond to Pt(0), Pd(0), or Ni(0) centers, see: (a) Jasaka, C. A.; Dorn, H.; Lough, A. N.; Manners, L. Chem. Eur. J. 2003, 9, 271. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (c) Gianandrea, R.; Mastrorilly, R.; Nolill, C. F.; Englert, U. J. Chem. Soc., Dalton Trans. 1997, 1355. (d) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, 2001; Chapter 5 and references therein.
31. For oxidative addition of phosphanes and phosphane oxides P-H bond to Pt(0), Pd(0), or Ni(0) centers, see: (a) Jasaka, C. A.; Dorn, H.; Lough, A. N.; Manners, L. Chem. Eur. J. 2003, 9, 271. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (c) Gianandrea, R.; Mastrorilly, R.; Nolill, C. F.; Englert, U. J. Chem. Soc., Dalton Trans. 1997, 1355. (d) Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, 2001; Chapter 5 and references therein.
32. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
33. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
34. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
35. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
36. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
37. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
38. For oxidative addition of E-Hal bond, see for example: (a) Kuyper, J. Inorg. Chem. 1977, 16, 2171. (b) Kuyper, J. Inorg. Chem. 1978, 17, 77. (c) Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1978, 144, 23. (d) Yamashita, H.; Hayashi, T.; Kobayashi, T.; Tanaka, M.; Goto, M. J. Am. Chem. Soc. 1988, 110, 4417. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834. (g) Yang, F.-Y.; Cheng, Ch.-H. J. Am. Chem. Soc. 2001, 123, 761.
39. Cecconi, F.; Ghilardi, C. A.; Midollini, S.; Moneti, S.; Orlandini, A.; Scapacci, G. Inorg. Chim. Acta 1991, 189, 105.
40. Bitterer, F.; Brauer, D. J.; Doerrenbach, F.; Gol, F.; Knueppel, P. C.; Stelzer, O.; Krueger, C.; Tsay, Y. H. Z. Naturforsch. B 1991, 46, 1131.
41. Ager, D. J.; East, M. B.; Eisenstadt, A.; Laneman, S. A. Chem. Commun. 1997, 2359.
42. Rolland, H.; Potin, P.; Majoral, J.-P.; Bertrand, J. Tetrahedron Lett. 1992, 33, 8095.