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

Chemical Communications

Volumn , Issue 15, 1997, Pages 1393-1394

  Bricout, Hervé ^a   Carpentier, Jean François ^a   Mortreux, André ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002668026     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702954c     Document Type: Article

References (12)

1. (a) H. Bricout, J.-F. Carpentier and A. Mortreux, Tetrahedron Lett., 1997, 38, 1053;
2. (b) Y. I. M. Nilsson, P. G. Andersson and J.-E. Bäckvall, J. Am. Chem. Soc., 1993, 115, 6609.
3. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
4. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
5. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
6. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
7. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
8. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
9. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
10. Palladium-catalysed nucleophilic substitution of allylamines and related derivatives: (a) K. E. Atkins, W. E. Walker and R. M. Manyik, Tetrahedron Lett., 1970, 43, 3821; (b) B. M. Trost and E. Keinan, J. Org. Chem., 1980, 45, 2741; (c) A. Hosomi, K. Hoashi, S. Kohra, Y. Tominaga, K. Otaka and H. Sakurai, J. Chem. Soc., Chem. Commun., 1987, 570; (d) F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109; (e) S. Murahashi, Y. Imada and K. Nishimura, Tetrahedron, 1994, 50, 453; (f) M. Grellier, M. Pfeffer and G. Van Koten, Tetrahedron Lett., 1994, 35, 2877; (g) S. Lemaire-Audoire, M. Savignac, J.-P. Genêt and J.-M. Bernard, Tetrahedron Lett., 1995, 36, 1267; (h) S. Lemaire-Audoire, M. Savignac, C. Dupuis and J.-P. Genêt, Bull. Soc. Chim. Fr., 1995, 132, 1157.
11. To the best of our knowledge, the cross-coupling of ally lamines 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.
12. H. Bricout, J.-F. Carpentier and A. Mortreux, J. Chem. Soc., Chem. Commun., 1995, 1863.