Elsevier

Tetrahedron Letters

Volume 38, Issue 36, 8 September 1997, Pages 6355-6358
Tetrahedron Letters

Ni(II)/Cr(II)-Mediated Coupling Reaction: Beneficial Effects of 4-tert-Butylpyridine as an Additive and Development of New and Improved Workup Procedures

https://doi.org/10.1016/S0040-4039(97)01462-7Get rights and content

Abstract

4-tert-Butylpyridine has been shown to be a beneficial additive in the Ni(II)/Cr(II)-mediated coupling reaction. This additive allows for homogeneous reactions, improves reproducibility, and inhibits homo-coupling of vinyl iodides or triflates. Improved workup procedures using chromium ion chelators (ethylenediamine or sodium or potassium serinate) allow for a better mass recovery. © 1997 Elsevier Science Ltd.

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Acknowledgements

Financial support from the National Institutes of Health (CA-22215) and Eisai Pharmaceutical Company is gratefully acknowledged.

References (14)

  • (a) Jin, H.; Uenishi, J-I.; Christ, W.J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644–5646. (b) Takai, K.; Tagashira,...
  • For some representative examples, see: Kishi, Y. Pure and Appl. Chem. 1989, 61, 313–324 and references cited...
  • For more recent synthetic efforts on halichondrins from this laboratory, see: (a) Stamos, D.P.; Kishi, Y. Tetrahedron...
  • For synthetic work from other laboratories, see: (a) Cooper, A.J.; Pan, W.; Salomon, R.G. Tetrahedron Lett. 1993, 34,...
  • For a new synthetic route to the C.14–C.38 segment of halichondrin through this type of intermediates, see the...
  • The vinyl iodide 2 was used as a 3:2 mixture of E- and Z-unsaturated esters. In the corresponding methyl ester series,...
  • C Chen et al.

    J. Org. Chem.

    (1995)
There are more references available in the full text version of this article.

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