Synthesis of 2,2′-biimidazolium-based ionic liquids: Use as a new reaction medium and ligand for palladium-catalyzed Suzuki cross-coupling reactions

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3072-3078

  Xiao, Ji Chang ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CROSSLINKING; IONIC CONDUCTION; PALLADIUM; REACTION KINETICS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

CATALYTIC IONIC LIQUIDS; ELECTROPHILES; METATHESIS REACTIONS; SUZUKI CROSS-COUPLING REACTIONS;

NITROGEN COMPOUNDS;

1,3,1' TRIBUTYL 2,2' BIIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 2,2' BIIMIDAZOLIUM; IMIDAZOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ANION EXCHANGE; ARTICLE; CATALYSIS; LIGAND BINDING; RING CLOSING METATHESIS; ROOM TEMPERATURE; SCANNING TUNNELING MICROSCOPY; SOLVENT EFFECT; STOICHIOMETRY; SUZUKI REACTION; SYNTHESIS; THERMOGRAVIMETRY;

EID: 17444363754     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0501083     Document Type: Article

References (32)

1. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
2. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
3. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
4. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
5. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
6. For recent review, see, for example: (a) Ionic Liquids as Green Solvents; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003. (b) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003. (c) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (e) Rogers, S. Chem. Commun. 2001, 2399-2407. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
7. For example, see: (a) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705-708. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26. (c) Müller, L. A.; Dupont, J.; de Souza, R. F. Macromol. Rapid Commun. 1998, 19, 409-411. (d) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132-1138. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233-236.
8. For example, see: (a) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705-708. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26. (c) Müller, L. A.; Dupont, J.; de Souza, R. F. Macromol. Rapid Commun. 1998, 19, 409-411. (d) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132-1138. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233-236.
9. For example, see: (a) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705-708. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26. (c) Müller, L. A.; Dupont, J.; de Souza, R. F. Macromol. Rapid Commun. 1998, 19, 409-411. (d) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132-1138. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233-236.
10. For example, see: (a) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705-708. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26. (c) Müller, L. A.; Dupont, J.; de Souza, R. F. Macromol. Rapid Commun. 1998, 19, 409-411. (d) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132-1138. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233-236.
11. For example, see: (a) Dyson, P. J.; Ellis, D. J.; Welton, T. Can. J. Chem. 2001, 79, 705-708. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26. (c) Müller, L. A.; Dupont, J.; de Souza, R. F. Macromol. Rapid Commun. 1998, 19, 409-411. (d) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132-1138. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233-236.
12. Boovanahalli, S. K.; Kim, D. W.; Chi, D. Y. J. Org. Chem. 2004, 69, 3340-3344.
13. Gu, Y.; Shi, F.; Deng, Y. J. Org. Chem. 2004, 69, 391-394.
14. (a) Singh, R. P.; Shreeve, J. M. Inorg. Chem. 2003, 42, 7416-7421.
15. (b) Singh, R. P.; Shreeve, J. M. Chem. Commun. 2003, 1366-1367.
16. Thummel, R. P.; Goulle, V.; Chen, B. J. Org. Chem. 1989, 54, 3057-3061.
17. Xiao, J.-C.; Twamley, B.; Shreeve, J. M. Org. Lett. 2004, 6, 3845-3847.
18. Cho, J. R.; Cho, S. G.; Goh, E. M.; Kim, J. K. FR2838440.
19. (a) Dupont, J.; Silva, S. M.; de Souza, R. F. Catal. Lett. 2001, 77, 131-133.
20. (b) Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451-452.
21. (a) Kottsieper, K. W.; Stelzer, O.; Wasserscheid, P. J. Mol. Catal. A: Chem. 2001, 175, 285-288.
22. (b) Zhao, D.; Fei, Z.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2004, 43, 2197-2205.
23. (c) Audic, N.; Claveier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248-9249.
24. (d) Zhao, D.; Fei, Z.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 15876-15882.
25. For reviews, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (d) Suzuki, A.; Brown, H. C.; Organic Syntheses via Boranes; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; Vol. 3, Suzuki Coupling.
26. For reviews, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (d) Suzuki, A.; Brown, H. C.; Organic Syntheses via Boranes; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; Vol. 3, Suzuki Coupling.
27. For reviews, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (d) Suzuki, A.; Brown, H. C.; Organic Syntheses via Boranes; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; Vol. 3, Suzuki Coupling.
28. For reviews, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (d) Suzuki, A.; Brown, H. C.; Organic Syntheses via Boranes; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; Vol. 3, Suzuki Coupling.
29. Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209-3212.
30. Terao, Y.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2004, 69, 6942-6944.
31. Li, J.-H.; Liu, W.-J.; Org. Lett. 2004, 6, 2809-2811.
32. Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421-1424.