Rate enhancement of the Morita–Baylis–Hillman reaction through mechanochemistry

Green Chemistry

Volumn 9, Issue 4, 2007, Pages 328-33

  Mack, James ^a   Shumba, Maxwell ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34047094942     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b612983h     Document Type: Article

References (33)

1. K. Tanaka, Solvent-free Organic Synthesis, Wiley-VCH, Cambridge, 2003.
2. K. Tanaka F. Toda Chem. Rev. 2000 100 1025-1074.
3. G. Rothenberg A. P. Downie C. L. Raston J. L. Scott J. Am. Chem. Soc. 2001 123 8701-8708.
4. C. Suryanarayana Prog. Mater. Sci. 2000 46 1-184.
5. L. Takacs Prog. Mater. Sci. 2002 47 355-414.
6. G. Kaupp Top. Curr. Chem. 2005 254 95-183.
7. V. P. Balema J. W. Wiench M. Pruski V. K. Pecharsky Chem. Commun. 2002 724-725.
8. V. P. Balema J. W. Wiench M. Pruski V. K. Pecharsky J. Am. Chem. Soc. 2002 124 6244-6245.
9. K. Komatsu G.-W. Wang Y. Murata T. Tanaka K. Fujiwara K. Yamamoto M. Saunders J. Org. Chem. 1998 63 9358-9366.
10. K. Komatsu K. Fujiwara Y. Murata Chem. Commun. 2000 1583-1584.
11. K. Komatsu K. Fujiwara Y. Murata T. Braun J. Chem. Soc., Perkin Trans. 1 1999 2963-2966.
12. K. Komatsu Y. Murata G.-W. Wang T. Tanaka N. Kato K. Fujiwara Fullerene Sci. Technol. 1999 7 609-620.
13. A. B. Baylis and M. E. D. Hillman, German Pat. 2155113, 1972.
14. A. B. Baylis and M. E. D. Hillman, Chem. Abs., 1972, 77, 34174q.
15. K. Morita Z. Suzuki H. Hirose Bull. Chem. Soc. Jpn. 1968 41 2815.
16. S. Zhu T. H. Hudson D. E. Kyle A. J. Lin J. Med. Chem. 2002 45 3491-3496.
17. M. P. Feltrin W. P. Almeida Synth. Commun. 2003 33 1141-1146.
18. P. J. Dunn M. L. Hughes P. M. Searle A. S. Wood Org. Process Res. Dev. 2003 7 244-253.
19. For comprehensive reviews see: D. Basavaiah A. J. Rao T. Satyanarayana Chem. Rev. 2003 103 811-891.
20. D. Basavaiah P. D. Rao R. S. Hyma Tetrahedron 1996 52 8001-8062.
21. E. Ciganek, Organic Reactions, ed. L.A. Paquette, Wiley, New York, 1997, vol. 51, p. 201.
22. S. E. Drewes G. H. P. Roos Tetrahedron 1988 44 4653-4670.
23. K. E. Price S. J. Broadwater B. J. Walker D. T. McQuade J. Org. Chem. 2005 70 3980-3987.
24. K. E. Price S. J. Broadwater H. M. Jung D. T. McQuade Org. Lett. 2005 7 147-150.
25. V. K. Aggarwal S. Y. Fulford G. C. Lloyd-Jones Angew. Chem., Int. Ed. 2005 44 1706-1708.
26. M. E. Krafft T. F. N. Haxell K. A. Seibert K. A. Abboud J. Am. Chem. Soc. 2006 128 4174-4175.
27. Y. Fort M. C. Berthe P. Caubere Tetrahedron 1992 48 6371-6384.
28. T. Kataoka H. Kinoshita T. Iwama S. I. Tsujiyama T. Iwamura S. I. Watanabe O. Muraoka G. Tanabe Tetrahedron 2000 56 4725-4731.
29. L. S. Santos C. H. Pavam W. P. Almeida F. Coelho M. N. Eberlin Angew. Chem., Int. Ed. 2004 43 4330-4333.
30. M. Shi C.-Q. Li J.-K. Jiang Tetrahedron 2003 59 1181-1189.
31. At the conclusion of ball milling, the crude product was dissolved in a minimal amount of methylene chloride and subjected to a 10% HCl wash. The organic layer was removed under reduced pressure and prepared for chromatography. Additional details can be obtained in the ESI.
32. R. Galeazzi G. Martelli G. Mobbili M. Orena S. Rinaldi Org. Lett. 2004 6 2571-2574.
33. D. Nilov R. Racker O. Reiser Synthesis 2002 2232-2242.