Exploration of Ionic Liquids as Soluble Supports for Organic Synthesis. Demonstration with a Suzuki Coupling Reaction

Organic Letters

Volumn 5, Issue 26, 2003, Pages 5003-5005

  Miao, Weishi ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; BORONIC ACID DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; METHANOL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; PURIFICATION; REACTION ANALYSIS; SUZUKI REACTION; TEMPERATURE SENSITIVITY;

EID: 0347916940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035977y     Document Type: Article

References (38)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. Bayer, E.; Mutter, M. Nature 1972, 237, 512.
3. Bonora, G. M.; Scremin, C. L.; Colonna, F. P. Nucleic Acids Res. 1990, 18, 3155.
4. Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1991, 113, 5095.
5. For leading references, see: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
6. For leading references, see: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
7. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
8. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
9. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
10. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
11. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
12. For leading references, see: (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. (c) Horvath, I. T. Acc. Chem. Res. 1998, 31, 641. (d) Betzemeier, B.; Knochel, P. Top. Curr. Chem. 1999, 206, 61. (e) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (f) Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
13. For recent reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Wilkes, J. S. Green Chem. 2002, 4, 73. (d) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
14. For recent reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Wilkes, J. S. Green Chem. 2002, 4, 73. (d) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
15. For recent reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Wilkes, J. S. Green Chem. 2002, 4, 73. (d) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
16. For recent reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Wilkes, J. S. Green Chem. 2002, 4, 73. (d) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
17. (a) Sheldon, R. Chem. Commun. 2001, 2399.
18. (b) Sheldon, R. A.; Lau, R. M.; Sorgedrager, M. J.; v. Rantwijk, F.; Seddon, K. R. Green Chem. 2002, 4, 147.
19. (a) Fuller, J.; Osteryoung, R. A. J. Electrochem. Soc. 1997, 144, 3881.
20. (b) Fuller, J.; Breda, A. C.; Carlin, T. J. Electroanal Chem. 1998, 459, 29.
21. (a) Huddleston, J. G.; Willauer, H.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 2001, 1765.
22. (b) Bosmann, A.; Datsevich, L.; Jess, A.; Lauter, A.; Schmitz, C.; Wasserscheid, P. Chem. Commun. 2001, 2494.
23. Ye, C.; Liu, W.; Chen, Y.; Yu. L. Chem. Commun. 2001, 2244.
24. (a) Kimizuka, N.; Nakashima, T. Langmuir 2001, 17, 6759.
25. (b) For other ionic liquids containing PEG, see: Leone, A. M.; Weatherly, S. C.; Williams, M. E.; Thorp, H. H.; Murray, R. W. J. Am. Chem. Soc. 2001, 123, 318.
26. The use of ionic liquid supported synthesis has been reported, but its advantage over conventional liquid-phase synthesis has not been demonstrated. See: (a) Fraga-Dubreuil, J.; Bazureau, J.; Bazureau, J. P. Tetrahedron Lett. 2001, 42, 6097. (b) Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron 2003, 59, 6121.
27. The use of ionic liquid supported synthesis has been reported, but its advantage over conventional liquid-phase synthesis has not been demonstrated. See: (a) Fraga-Dubreuil, J.; Bazureau, J.; Bazureau, J. P. Tetrahedron Lett. 2001, 42, 6097. (b) Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron 2003, 59, 6121.
28. For recent reports of Suzuki reaction in water and in ionic liquids, see: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (d) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
29. For recent reports of Suzuki reaction in water and in ionic liquids, see: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (d) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
30. For recent reports of Suzuki reaction in water and in ionic liquids, see: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (d) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
31. For recent reports of Suzuki reaction in water and in ionic liquids, see: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (d) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
32. For recent reports of Suzuki reaction in water and in ionic liquids, see: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. (d) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
33. (a) Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
34. (b) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
35. (c) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885.
36. (d) Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
37. Branco, L. C.; Rosa, J. N.; Moura Ramos, J. J.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
38. Methyl p-iodobenzoate was not observed in the final product under the reaction conditions. Separate experiments showed that any unreacted 5 would have been recovered as methyl p-iodobenzoate. The less than 100% yield of 3a was attributed to mechanical loss in the work up process.