Ni(acac)2-catalyzed cross-coupling and carbonylative cross-coupling of organostannanes with hypervalent iodonium salts

(Note: The full text of this document is currently only available in the PDF Version )

Suk-Ku Kang, Hyung-Chul Ryu and Sang-Woo Lee


Abstract

The Ni-catalyzed cross-coupling and carbonylative cross-coupling of organostannanes with hypervalent iodonium salts were achieved in the presence of Ni(acac)2 (10 mol%) in NMP at 70 °C in moderate yields.


References

  1. Review: (a) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508 CrossRef; (b) T. N. Mitchell, Synthesis, 1992, 803 CrossRef CAS.
  2. (a) J. R. Falck, R. K. Bhatt and J. Ye, J. Am. Chem. Soc., 1996, 117, 5973–5982; (b) S.-K. Kang, J.-S. Kim and S.-C. Choi, J. Org. Chem., 1997, 62, 4208–4209 CrossRef CAS.
  3. (a) R. M. Moriarty and W. R. Epa, Tetrahedron Lett., 1992, 33, 4095–4008 CrossRef CAS; (b) R. T. Hinkle, G. T. Poulter and P. J. Stang, J. Am. Chem. Soc., 1993, 115, 11626–11627 CrossRef CAS; (c) S.-K. Kang, H.-W. Lee, J.-S. Kim and S.-C. Choi, Tetrahedron Lett., 1996, 37, 3733–3736; (d) S.-K. Kang, H.-W. Lee, S.-B. Jang, T.-H. Kim and J.-S. Kim, Synth. Commun., 1996, 26, 4311–4318 CAS.
  4. S.-K. Kang, T. Yamaguchi, T.-H. Kim and P.-S. Ho, J. Org. Chem., 1996, 61, 9082–9083 CrossRef CAS.
  5. V. Percec, J.-Y. Bae and D. H. Hill, J. Org. Chem., 1995, 60, 6895–6903 CrossRef CAS.
  6. A. F. Indolese, Tetrahedron Lett., 1997, 38, 3513–3516 CrossRef CAS.
  7. (a) T. Sotoyama, S. Hara and A. Suzuki, Bull. Chem. Soc. Jpn., 1979, 52, 1865–1866 CAS; (b) E. I. Negishi, F. T. Luo, R. Frishee and H. Matsushita, Heterocycles, 1992, 22, 1667–1669.
  8. A. Pelter, M. Rowland and G. Clements, Synthesis, 1987, 51–53 CrossRef.
  9. L. T. Baldwin, S. Pakray, R. Castle and M. L. Lee, J. Heterocycl. Chem., 1985, 22, 1667–1669 CAS.
  10. S.-K. Kang, K.-H. Lim, P.-S. Ho, S.-K. Yoon and H.-J. Son, Synth. Commun., 1998, 28, 1481–1489 CAS.
  11. L. Delaude, A. M. Masdeu and H. Alper, Synthesis, 1994, 1149–1151 CrossRef CAS.
  12. T. Kobayashi and M. Tanaka, J. Chem. Soc., Chem. Commun., 1981, 333–334 RSC.
  13. M. A. Ciafolin and N. E. Byrne, J. Chem. Soc., Chem. Commun., 1988, 1230–1231 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.