Preparation of vicinal diimines: a new dehydrogenative coupling reaction of aldimines mediated by ytterbium metal

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

Wu-Song Jin and Yuki Taniguchi


Abstract

Dehydrogenative coupling takes place to give vicinal diimine compounds in the reaction of aromatic aldimines with ytterbium metal followed by treatment with aromatic aldehydes such as 1-naphthaldehyde (1-NpCHO) as a hydrogen acceptor.


References

  1. T. Imamoto, Lanthanides in Organic Synthesis, Academic Press, London, 1994, pp. 7–19 Search PubMed; Y. Fujiwara, K. Takaki and Y. Taniguchi, J. Alloys Compd., 1993, 192, 200 Search PubMed.
  2. For example, Z. Hou, K. Takamine, K. Aoki, O. Shiraishi, Y. Fujiwara and H. Taniguchi, J. Org. Chem., 1988, 53, 6077 Search PubMed; Z. Hou, H. Yamazaki, K. Kobayashi, Y. Fujiwara and H. Taniguchi, J. Chem. Soc., Chem. Commun., 1992, 722 CrossRef CAS; K. Takaki, F. Beppu, S. Tanaka, Y. Tsubaki, T. Jintoku and Y. Fujiwara, J. Chem. Soc., Chem. Commun., 1990, 516 RSC; Y. Makioka, S. Uebori, M. Tsuno, Y. Taniguchi, K. Takaki and Y. Fujiwara, Chem. Lett., 1994, 611 RSC; Y. Makioka, M. Tsuno, S. Ueboki, Y. Taniguchi, K. Takaki and Y. Fujiwara, J. Org. Chem., 1996, 61, 372 CAS.
  3. K. Takaki, Y. Tsubaki, S. Tanaka, F. Beppu and Y. Fujiwara, Chem. Lett., 1990, 203; K. Takaki, S. Tanaka and Y. Fujiwara, Chem. Lett., 1991, 493; Y. Taniguchi, T. Kuno, M. Nakahashi, K. Takaki and Y. Fujiwara, J. Alloys Compd., 1994, 216, L9–12 CrossRef CAS; Y. Taniguchi, T. Kuno, M. Nakahashi, K. Takaki and Y. Fujiwara, Appl. Organomet. Chem., 1995, 9, 491 CrossRef CAS.
  4. T. Imamoto and S. Nishimura, Chem. Lett., 1990, 1141 CAS; E. J. Enholm, D. C. Forbes and D. P. Holub, Synth. Commum., 1990, 20, 981 Search PubMed; A. Lebrun, E. Rantze, J.-L. Namy and H. B. Kagan, New J. Chem., 1995, 19, 699 Search PubMed.
  5. Y. Makioka, Y. Taniguchi, Y. Fujiwara, K. Takaki, Z. Hou and Y. Wakatsuki, Organometallics, 1996, 15, 5476 CrossRef CAS.
  6. J. G. Smith and I. Ho, J. Org. Chem., 1972, 37, 653 CrossRef CAS.
  7. C. Djerassi, Org. React., 1951, 6, 207.
Click here to see how this site uses Cookies. View our privacy policy here.