Palladium catalysed heck reactions and allylic substitution reactions using glass bead technology

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4319-4322

  Tonks, Louise ^a   Anson, Michael S ^c   Hellgardt, Klaus ^b   Mirza, Amin R ^a   Thompson, David F ^a   Williams, Jonathan M J ^a  

^a UNIVERSITY OF BATH   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYST; DRUG SYNTHESIS; IN VITRO STUDY; TECHNIQUE;

EID: 0030996032     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00890-3     Document Type: Article

References (12)

1. For a review on supported aqueous phase catalysis, see; M. E. Davis, Chemtech, 1992, 498-502.
2. J. P. Arhancet, M. E. Davis, J. S. Merola and B. E. Hanson, Nature, 1989, 339, 454-455. For a related asymmetric version, see; K. T. Wan and M. E. Davis, Nature, 1994, 370, 449-450.
3. J. P. Arhancet, M. E. Davis, J. S. Merola and B. E. Hanson, Nature, 1989, 339, 454-455. For a related asymmetric version, see; K. T. Wan and M. E. Davis, Nature, 1994, 370, 449-450.
4. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73-77. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325-2330.
5. For examples of Heck reactions using water-soluble ligands, see, J. Kiji, T. Okano and T. Hasegawa, J. Mol. Cat. A, 1995, 97, 73-77. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325-2330.
6. The use of fewer equivalents of ligand afforded higher levels of leaching.
7. Controlled pore glass beads are commercially available (Cambio). We are grateful to GlaxoWellcome for purchasing these beads on our behalf.
8. Freeze drying was performed on an Edwards Modulyo Pirani 10 Freezedrier
9. Leaching of palladium was determined as follows: The decanted samples were filtered and furnaced at 400°C, and extracted into 3 drops of aqua regia and 3mL deionised water added. Samples were analysed on a Perkin Elmer 1100B atomic absorption instrument in conjunction with a series of Pd standards.
10. J. B. Melpolder and R. F. Heck, J. Org. Chem. 1976, 41, 265.
11. E. Fache, C. Mercier, N. Pagnier, B. Despeyroux and P. Panster, J. Mol. Catal., 1993, 79, 117
12. During the course of this work, the use of silica-supported aqueous phase palladium catalysed allylic substitution has been reported. P. Schneider, F. Quignard, A. Choplin and D. Sinou, New J. Chem., 1996, 20, 545.