Efficient coupling reactions of allylamines with soft nucleophiles using nickel-based catalysts

Abstract

Substitution reactions of N,N-diethylallylamine 1 with soft nucleophiles such as active methylene compounds 2a–c and piperidine 5 proceed much more rapidly in the presence of Ni(dppb)₂ [dppb = 1,4-bis(diphenylphosphino)butane] as catalyst than with comparable palladium systems.

References

1. (a) H. Bricout, J.-F. Carpentier and A. Mortreux, Tetrahedron Lett., 1997, 38, 1053; (b) Y. I. M. Nilsson, P. G. Andersson and J.-E. Bäckvall, J. Am. Chem. Soc., 1993, 115, 6609.
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3. To the best of our knowledge, the cross-coupling of allylamines with boronic acids (‘hard’ nucleophiles) is the sole example of the use of nickel catalysts: B. M. Trost and M. D. Spagnol, J. Chem. Soc., Perkin Trans. 1, 1995, 2083.
4. H. Bricout, J.-F. Carpentier and A. Mortreux, J. Chem. Soc., Chem. Commun., 1995, 1863.