CuI.PPh3 Based Functionalized Aromatic Organocopper Reagents Efficient in the Formation of Carbon-Carbon Bond with Epoxides

Authors

  • Santosh S. Devkate  S.M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Arvind S. Burungale  S.M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Sunil D. Jadhav  S.M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ashok S. Pise  S.M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ramesh B. Gawade  S.M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Mohan B. Kale  S.M. Joshi College Hadapsar, Pune, Maharashtra, India

Keywords:

Lithium napthalenide, active copper, triphenyl phosphine, napthalene, zero valent

Abstract

We have observed that the lithium napthalenide reduction of solution of CuI.PPh3 complex produced a highly reactive zero valent copper complex. The choice of phosphine based ligand was found to be crucial for the formation of subsequent reactivity of the organocopper species. The aromatic copper reagents derived from aromatic halides reacts with epoxides to form carbon carbon bond which are synthetically useful.

References

  1. Suzuki, Y.; Suzuki, T.; Kawagish, T.; Noyori, R.; Tetrahedron Letters, 1980, 21, 1247.
  2. Ebert, G. W.; Rieke, R. D.; J. Org. Chem.,1984, 49, 5280.
  3. Smith, J. G.; Synthesis, 1984, 629.
  4. Stark,G.; Cohen, J. F.; J. Am. Chem. Soc., 1974, 96, 5270.
  5. Stark, G.; Cama, L. D.; Coulson, D. R.; J. Am. Chem. Soc., 1974, 96, 5268.
  6. Hodgson, D. M.; Robinson, L. A.; Jones, M. L.; Tetrahedron Letters, 1999, 40, 8637.
  7. Reddy, L. R.; Reddy, M. A.; Chanumathi, N.; Rao, K. R. Synlett, 2000, 339.
  8. Sabitha, G,; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S.; Synthesis, 2003, 2298.
  9. Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mechiorre, P.; Sambri, L.; Org Lett. 2004, 6, 3973.
  10. Zhao, P. Q.; Xu, L. W.; Xia, C. G.; Synlett, 2004, 846.
  11. Fink, D. M.; Synlett, 2004, 2394.
  12. Iranpoor, N.; Kazemi, F.; Synth. Commun., 1999, 29, 561.
  13. Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S.; Org. Lett., 2002, 4, 343.
  14. Kalita, B.; Barua, N. C.; Bezbarua, M.; Bez, G.; Synlett., 2001, 1411.
  15. Fujiwara, M.; Tanaka, M,; Baba, A,; Ando, H.; Souma, Y.; Tetrahedron Letters, 1995, 36, 4849.
  16. Campbell, J. R.; Jones, J. K. N.; Wolfe, S.; Can. J. Chem., 1966, 44, 2339.
  17. Isaacs, N. S.; Kirkpatrick, D.; Tetrahedron Letters, 1972, 3869.
  18. Baldwin, J. E.; J. Chem. Soc. Chem. Commun. 1976, 734.
  19. Sartillo-Piscil, F.; Quinero, L.; Villegas, C.; Santacruz Juarez, E.; de Parrrodi, C. A.; Tetrahedron Letters, 2002, 43, 15.
  20. Harder, S.; Vanlenthe, J. H.; Van Eikkema Hommes, N. J. R.; Schleyer, P. V. R.; J. Am. Chem. Soc., 1994, 116, 2508.
  21. Rieke, R. D.; Rhyne, L. D.; J. Org. Chem., 1984, 49, 3445.
  22. Rieke, R. D.; CRC Crit. Rev. Surf. Chem., 1991, 1, 131.
  23. Rieke, R. D.; Science, 1989, 246, 12160.

International Journal of Scientific Research in Science and Technology

Downloads

Published

2017-12-31

Issue

Volume 3, Issue 8, November-December-2017

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
Santosh S. Devkate, Arvind S. Burungale, Sunil D. Jadhav, Ashok S. Pise, Ramesh B. Gawade, Mohan B. Kale, " CuI.PPh3 Based Functionalized Aromatic Organocopper Reagents Efficient in the Formation of Carbon-Carbon Bond with Epoxides, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 3, Issue 8, pp.998-1001, November-December-2017.