Polymer-supported distannanes: A new and efficient synthesis of highly effective reagents for iodine atom transfer cyclisations

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 831-834

  Hernán, Alejandro G ^a   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Atom transfer; Distannane; Polymer supported

Indexed keywords

CARBON 13; IODINE; POLYMER; TIN;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DEHYDROGENATION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0348048820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.039     Document Type: Article

References (31)

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7. For example, tris(trimethylsilyl)silane: Chatgilialoglu C. Acc. Chem. Res. 25:1992;188-194. hypophosphite salts: Barton D.H.R., Jang D.O., Jaszberenyi J.Cs. J. Org. Chem. 58:1993;6838-6842 Graham S.R., Murphy J.A., Coates D. Tetrahedron Lett. 40:1999;2415-2416.
8. Water soluble: Clive D.L.J., Waing J. J. Org. Chem. 67:2002;1192-1198. acid soluble: Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 Vedejs E., Duncan S.M., Haight A.R. J. Org. Chem. 58:1993;3046-3048. fluorous: Curran D.P., Hadida S., Kim S.Y., Luo Z.Y. J. Am. Chem. Soc. 121:1999;6607-6615.
9. Water soluble: Clive D.L.J., Waing J. J. Org. Chem. 67:2002;1192-1198. acid soluble: Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 Vedejs E., Duncan S.M., Haight A.R. J. Org. Chem. 58:1993;3046-3048. fluorous: Curran D.P., Hadida S., Kim S.Y., Luo Z.Y. J. Am. Chem. Soc. 121:1999;6607-6615.
10. Water soluble: Clive D.L.J., Waing J. J. Org. Chem. 67:2002;1192-1198. acid soluble: Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 Vedejs E., Duncan S.M., Haight A.R. J. Org. Chem. 58:1993;3046-3048. fluorous: Curran D.P., Hadida S., Kim S.Y., Luo Z.Y. J. Am. Chem. Soc. 121:1999;6607-6615.
11. Water soluble: Clive D.L.J., Waing J. J. Org. Chem. 67:2002;1192-1198. acid soluble: Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 Vedejs E., Duncan S.M., Haight A.R. J. Org. Chem. 58:1993;3046-3048. fluorous: Curran D.P., Hadida S., Kim S.Y., Luo Z.Y. J. Am. Chem. Soc. 121:1999;6607-6615.
12. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
13. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
14. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
15. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
16. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
17. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
18. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
19. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
20. See, for example, Gerigk U., Gerlach M., Neumann W.P., Vieler R., Weintritt V. Synthesis. 1990;448-452 Kuhn H., Neumann W.P. Synlett. 1994;123-124 Dumartin G., Kharboutli J., Delmond B., Pereyre M., Biesemans M., Gielen M., Willem R. Organometallics. 15:1996;19-23 Chemin A., Deleuze H., Maillard B. Eur. Polym. J. 34:1998;1395-1404 Nicolaou K.C., Winssinger N., Pastor J., Murphy F. Angew. Chem., Int. Ed. 37:1998;2534-2537 Enholm E.J., Schulte J.P. II Org. Lett. 1:1999;1275-1277 Enholm E.J., Gallagher M.E., Moran K.M., Lombardi J.S., Schulte J.P. II Org. Lett. 1:1999;689-691 Boussaguet P., Delmond B., Dumartin G., Pereyre M. Tetrahedron Lett. 41:2000;3377-3380 Zhu X., Blough B.E., Carroll F.I. Tetrahedron Lett. 41:2000;9219-9222.
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28. 6; 112 MHz): δ=-99.57 ppm; Microanalysis: Sn=14. 8% (1.25 mmol/g).
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31. Tin analysis was carried out by digesting the sample in acid followed by ICP (inductively coupled plasma) analysis, and was performed by Medac Ltd.