Real-time monitoring of microwave-promoted Suzuki coupling reactions using in situ Raman spectroscopy

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4589-4591

  Leadbeater, Nicholas E ^a   Smith, Rebecca J ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750086358     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061803f     Document Type: Article

References (30)

1. A number of books on microwave-promoted synthesis have been published recently: (a) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinhiem, 2005.
2. (b) Lidström, P.; Tierney, J. P., Eds. Microwave-Assisted Organic Synthesis; Blackwell: Oxford, 2005.
3. (c) Loupy, A., Ed. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
4. (d) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002.
5. For recent reviews, see: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
6. (b) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
7. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlain, A. R. J. Comb. Chem. 2002, 4, 95.
8. (c) Lidström, P.; Tierney, J. P.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
9. For a review, see: Leadbeater, N. E. Chem. Commun. 2005, 2881.
10. For other reports of microwave-promoted Suzuki couplings in water, see: (a) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885.
11. (b) Han, J. W.; Castro, J. C.; Burgess, K. Tetrahedron Lett. 2003, 44, 9359.
12. (c) Appukkuttan, P.; Orts, A.; Chandran, R. P.; Goeman, J. L.; Van der Eycken, J.; Dehaen, W.; Van der Eycken, E. Eur. J. Org. Chem. 2004, 3277.
13. (d) Gong, Y.; He, W. Org. Lett. 2002, 4, 3803.
14. (e) Namboodiri, V. V.; Varma, R. S. Green Chem. 2001, 3, 146.
15. (f) Zhang, W.; Chen, C. H.-T.; Lu, Y.; Nagashima, T. Org. Lett. 2004, 6, 1473.
16. (g) Solodenko, W.; Schön, U.; Messinger, J.; Glinschert, A.; Kirschning, A. Synlett 2004, 1699.
17. Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. S. J. Org. Chem. 2005, 70, 161.
18. (a) Arvela, R. K.; Leadbeater, N. E.; Mack, T. M.; Kormos, C. M. Tetrahedron Lett. 2006, 47, 217.
19. (b) Arvela, R. K.; Leadbeater, N. E. Org, Lett. 2005, 7, 2101.
20. (c) Arvela, R. K.; Leadbeater, N. E.; Collins, M. J. Tetrahedron 2005, 61, 9349.
21. Leadbeater, N. E.; Williams, V. A.; Barnard, T. M.; Collins, M. J. Org. Proc. Res. Dev. 2006, 10, 833.
22. Chanthavong, F.; Leadbeater, N. E. Tetrahedron Lett. 2005, 47, 1909.
23. For a review, see: Tompsett, G. A.; Conner, W. C.; Yngvesson, K. S. ChemPhysChem 2006, 7, 296.
24. Robb, G. R.; Harrison, A.; Whittaker, A. G. Phys. Chem. Commun. 2002, 135.
25. Dokter, W. H.; Beelen, T. P. M.; Vangarderen, H. F.; Vansanten, R. A.; Bras, W.; Derbyshire, G. E.; Mant, G. R. J. Appl. Crystallogr. 1994, 27, 901.
26. Yang, S. Y.; Navrotsky, A. Chem. Mater. 2004, 16, 3682.
27. Hocdé, S.; Pledel-Boussard, C.; Le Coq, D.; Fonteneau, G.; Lucas, J. Proc. SPIE-Int. Soc. Opt. Eng. 1999, 3849, 50.
28. Pivonka, D. E.; Empfield, J. R. Appl. Spectrosc. 2004, 58, 41.
29. Barnard, T. M.; Leadbeater, N. E. Chem. Commun. 2006, 3615.
30. This compares to a 1:1 ethanol/water mixture reported in ref 8.