Polymer-supported organotin reagents in the catalytic Stille reaction

Tetrahedron Letters

Volumn 44, Issue 47, 2003, Pages 8601-8603

  Hernán, Alejandro G ^a   Guillot, Vincent ^a   Kuvshinov, Alexander ^a   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Polymer supported; Stille reaction; Tin chloride

Indexed keywords

DIBUTYLTIN; DIMETHYLTIN CHLORIDE; ORGANOTIN COMPOUND; POLYMER; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STILLE REACTION; SYNTHESIS;

EID: 0142231037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.143     Document Type: Article

References (24)

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8. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
9. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
10. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
11. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
12. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
13. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
14. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
15. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
16. See for example: (a) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R. ; Weintritt, V. Synthesis 1990, 448-452; (b) Kuhn, H.; Neumann, W. P. Synlett 1994, 123; (c) Dumartin, G.; Kharboutli, J.; Delmond, B.; Pereyre, M.; Biesemans, M.; Gielen, M.; Willem, R. Organometallics 1996, 15, 19-23; (d) Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34, 1395-1404; (e) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537; (f) Enholm, E. J.; Schulte, J. P., II Org. Lett. 1999, 1, 1275-1277; (g) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P., II Org. Lett. 1999, 1, 689-691; (h) Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380; (i) Zhu, X.; Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 2000, 41, 9219-9222.
17. 2 in monoglyme: Birnbaum E.R., Javora P.H. J. Organomet. Chem. 9:1967;379-382.
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20. 4Sn.
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22. Alkynols were used as the alcohol functionality assisted in the purification of the products, but unfunctionalised alkynes can also be used: see Ref. 2.
23. Tin analysis was carried out by digesting the sample in sulphuric acid followed by ICP (Inductively Coupled Plasma) analysis, and was performed by Medac Ltd.
24. In practice the coupling and oxidative reactions of polymer-supported organotin reagents has been noted in several instances using resins with low crosslinking. For a discussion see Ref. 3d.