Palladium-catalyzed C-C coupling under thermomorphic conditions

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9058-9064

  Bergbreiter, David E ^a   Osburn, Philip L ^a   Wilson, Allan ^a   Sink, Erin M ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; LIGAND; MACROGOL; PALLADIUM; PHOSPHINE; POLY(N ISOPROPYLACRYLAMIDE); POLYMER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; MISCIBILITY; OXIDATION; PURIFICATION; REACTION ANALYSIS;

EID: 0034721443     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001708g     Document Type: Article

References (50)

1. Chen, S.; Janda, K. D. J. Am. Chem. Soc. 1997, 119, 8724.
2. Bergbreiter, D. E.; Zhang, L.; Mariagnanam, V. M. J. Am. Chem. Soc. 1993, 115, 9295.
3. Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843.
4. Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, 1996; Vol. 2.
5. (a) Starks, C. M.; Liotta, C. L.; Halpern, M., Eds. Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Chapman & Hall: New York, 1994.
6. (b) Mathias, L. J.; Carraher, C. E., Jr., Eds. Crown Ethers and Phase Transfer Catalysis in Polymer Science; Plenum Press: New York, 1984; Polymer Science and Technology, Vol. 24.
7. Keim, W. Chem. Eng. Technol. 1984, 56, 850.
8. Cornils, B. Org. Proc. Res. Dev. 1998, 2, 121.
9. Baker, R. T.; Tumas, W. Science 1999, 284, 1477.
10. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
11. (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron 2000, 56, 351.
12. (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 2000, 41, 57.
13. (c) Wipf, P.; Curran, D. P. Science 1997, 275, 823.
14. (a) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696.
15. (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995.
16. (c) Klose, A.; Gladysz, J. A. Tetrahedron: Asymmetry 1999, 10, 2665.
17. (a) Koch, D.; Leitner, W. J. Am. Chem. Soc. 1998, 720, 13398.
18. (b) Kling, R.; Sinou, D.; Pozzi, G.; Choplin, A.; Quignard, F.; Busch, S.; Kainz, S.; Koch, D.; Leitner, W. Tetrahedron Lett. 1998, 39, 9439.
19. (a) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945.
20. (b) Kleijn, H.; Rijnberg, E.; Jastrzebski, J. T. B. H.; van Koten, G. Org. Lett. 1999, 1, 853.
21. (a) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37.
22. (b) Barthel-Rosa, L. P.; Gladysz, J. A. Coord. Chem. Rev. 1999, 190-192, 587.
23. (c) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
24. Klement, I.; Lütjens, H.; Knochel, P. Angew. Chem., Int. Ed. 1997, 36, 1454.
25. (a) Carter, C. A. G.; Baker, R. T.; Tumas, W.; Nolan, S. P Chem. Commun. 2000, 5, 347.
26. (b) Pesiri, D. R.; Morita, D. K.; Walker, T.; Tumas, W. Organometallics 1999, 18, 4916.
27. (c) Jacobson, G. B.; Lee, C. T.; Johnston, K. P.; Tumas, W. J. Am. Chem. Soc. 1999, 121, 11902.
28. (a) Carson, T.; Lizotte, J.; Desimone, J. M. Macromolecules 2000, 33, 1917.
29. (b) Shiho, H.; Desimone, J. M. Macromolecules 2000, 33, 1565.
30. (c) Shiho, H.; Desimone, J. M. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1146.
31. Bergbreiter, D. E. Catal. Today 1998, 42, 389.
32. (a) Bergbreiter, D. E.; Franchina, J. G.; Koshti, N.; Frels, J.; Williams, L.; Case, B. L. Comb. Chem. High Throughput Screening 2000, 3, 153.
33. (b) Bergbreiter, D. E.; Franchina, J. G.; Case, B. L. Org. Lett. 2000, 2, 393.
34. (c) Bergbreiter, D. E.; Koshti, N.; Franchina, J. G.; Frels, J. D. Angew. Chem., Int. Ed. Engl. 2000, 39, 1040.
35. (d) Bergbreiter, D. E.; Franchina, J. G. Chem. Commun. 1997, 1531.
36. (a) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053.
37. (b) Case, B. L.; Franchina, J. G.; Liu, Y.-S.; Bergbreiter, D. E. Chem. Ind. 1998, 75, 403.
38. (c) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 3703.
39. (d) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843.
40. (e) Bergbreiter, D. E.; Weatherford, D. A. J. Org. Chem. 1989, 54, 2726.
41. Bergbreiter, D. E.; Liu, Y.-S.; Osburn, P. L. J. Am. Chem. Soc. 1998, 120, 4250.
42. Bianchini, C.; Frediani, P.; Sernau, V. Organometallics 1995, 14, 5458.
43. Francis, A. W. Critical Solution Temperatures; American Chemical Society: Washington, 1961.
44. (a) Zhao, F.; Shirai, M.; Arai, M. J. Mol. Catal. A: Chem. 2000, 154, 39.
45. (b) Zhao, F. Y.; Bhanage, B. M.; Shirai, M.; Arai, M. J. Mol. Catal. A: Chem. 1999, 142, 383.
46. (a) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531.
47. (b) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287.
48. (c) Dupont, J.; Beydon, N.; Pfeffer, M. J. Chem. Soc., Dalton Trans. 1989, 1715.
49. (d) Spencer, J.; Pfeffer, M.; Kyritsakas, N.; Fischer, J. Organometallics 1995, 14, 2214.
50. (e) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881.