Palladium-catalysed borylsilylation of alkynes and borylsilylative carbocyclization of diynes and an enyne compound

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

Shun-ya Onozawa, Yasuo Hatanaka and Masato Tanaka


Abstract

Addition reactions or addition–carbocyclization reactions of a borylsilane with alkynes, α,ω-diynes or an enyne compound proceed efficiently in the presence of palladium catalysts, P(OCH2)3CEt being the ligand of choice.


References

  1. For reviews, see Organometallic Reagents in Organic Synthesis, ed. J. H. Bateson and M. B. Mitchell, Academic Press, New York, 1994, pp. 129–160 Search PubMed; H. K. Sharma and K. H. Pannell, Chem. Rev., 1995, 95, 1351 Search PubMed.
  2. T. Ishiyama, N. Matsuda, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 11018 CrossRef CAS; R. T. Baker, P. Nguyen, T. B. Marder and S. A. Westcott, Angew. Chem., Int. Ed. Engl., 1995, 34, 1336 CrossRef CAS; T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki and N. Miyaura, Organometallics, 1996, 15, 713 CrossRef; G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg and N. C. Norman, Organometallics, 1996, 15, 5137 CrossRef; C. N. Iverson and M. R. Smith, III, Organometallics, 1996, 15, 5155 CrossRef CAS.
  3. T. Ishiyama, K.-i. Nishijima, N. Miyaura and A. Suzuki, J. Am. Chem. Soc., 1993, 115, 7219 CrossRef CAS; L.-B. Han, N. Choi and M. Tanaka, J. Am. Chem. Soc., 1996, 118, 7000 CrossRef CAS.
  4. S.-y. Onozawa, Y. Hatanaka, T. Sakakura, S. Shimada and M. Tanaka, Organometallics, 1996, 15, 5450 CrossRef CAS.
  5. (a) S.-y. Onozawa, Y. Hatanaka, T. Sakakura and M. Tanaka, presented at the 43rd Symposium on Organometallic Chemistry, Abstract PB231, Osaka, October 31–November 1st, 1996; (b) S.-y. Onozawa, Y. Hatanaka, T. Sakakura and M. Tanaka, presented at the 72nd Spring Annual Meeting of the Chemical Society of Japan, Abstract 3F146, Tokyo, March 27–30th, 1997.
  6. J. D. Buynak and B. Geng, Organometallics, 1995, 14, 3112 CrossRef CAS.
  7. M. Suginome, H. Nakamura, T. Matsuda and Y. Ito, presented at the 72nd Spring Annual Meeting of the Chemical Society of Japan, Abstract 2F226, Tokyo, March 27–30th, 1997.
  8. T. Hayashi, A. M. Kawamoto, T.-a. Kobayashi and M. Tanaka, J. Chem. Soc., Chem. Commun., 1990, 563 RSC.
  9. (a) H. Yamashita, M. Catellani and M. Tanaka, Chem. Lett., 1991, 241 CAS; (b) H. Yamashita and M. Tanaka, Chem. Lett., 1992, 1547 CAS; (c) T. Hayashi, H. Yamashita, T. Sakakura, Y. Uchimaru and M. Tanaka, Chem. Lett., 1991, 245 CAS; (d) H. Yamashita, N. P. Reddy and M. Tanaka, Macromolecules, 1993, 26, 2143 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.