Sterically demanding, zwitterionic trialkylphosphonium sulfonates as air-stable ligand precursors for efficient palladium-catalyzed cross-couplings of aryl bromides and chlorides

Synthesis

Volumn , Issue 12, 2008, Pages 1965-1970

  Brown, William S ^a   Boykin, D'Ariel D ^a   M Quentin Sonnier Jr , ^a   William D Clark, ^a   Brown, Fallon V ^a   Shaughnessy, Kevin H ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

Aqueous phase catalysis; Aryl halides; Cross coupling; Ligands; Palladium

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; FARM BUILDINGS; PALLADIUM; PROPANE;

4 CHLOROANISOLE; ACTIVE CATALYSTS; ARYL BROMIDES; LIGAND PRECURSORS; PALLADIUM CATALYZED CROSS COUPLING REACTIONS; PALLADIUM-CATALYZED CROSS-COUPLINGS; ROOM-TEMPERATURE (RT); SONOGASHIRA COUPLING; STERICALLY DEMANDING; SUZUKI COUPLINGS;

LIGANDS;

3 (DI TERT BUTYLPHOSPHONIUM)PROPANESULFONATE; 3 (DIADAMANTYLPHOSPHONIUM)PROPANESULFONATE; 4 CHLOROANISOLE; ALKYL GROUP; AMPHOLYTE; ANISOLE DERIVATIVE; BROMINE DERIVATIVE; CHLORIDE; HALIDE; LIGAND; PALLADIUM; PHOSPHONIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AIR; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; ROOM TEMPERATURE; SONOGASHIRA REACTION; STEREOCHEMISTRY;

EID: 46649092757     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067095     Document Type: Article

References (41)

1. (a) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
2. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
3. (a) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
4. (b) Hill, L. L.; Moore, L. R.; Huang, R.; Craciun, R.; Vincent, A. J.; Dixon, D. A.; Chou, J.; Woltermann, C. J.; Shaughnessy, K. H. J. Org. Chem. 2006, 71, 5117.
5. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc.2000, 122, 4020.
6. (d) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
7. (e) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
8. (f) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem. Int. Ed.2000, 39, 4153.
9. (a) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
10. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem.2000, 65, 1158.
11. (c) Kuwabe, S.-L.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202.
12. (d) Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 6523.
13. (e) Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Beller, M. Tetrahedron Lett. 2005, 46, 3237.
14. (f) Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Reiermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004, 10, 2983.
15. Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
16. (a) Kantchev, E. A. B.; O' Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007, 46, 2768.
17. (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
18. (c) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053.
19. (d) Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557.
20. (e) Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363.
21. (f) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101.
22. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889.
23. (a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
24. (b) Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
25. Miyaura, N.; Yangi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
26. Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324.
27. (a) Shaughnessy, K. H. Eur. J. Org. Chem. 2006, 1827.
28. (b) Shaughnessy, K. H.; DeVasher, R. B. Curr. Org. Chem. 2005, 9, 585.
29. DeVasher, R. B.; Spruell, J. M.; Dixon, D. A.; Broker, G. A.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H. Organometallics 2005, 24, 962.
30. DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919.
31. (a) Nishimura, M.; Ueda, M.; Miyaura, N. Tetrahedron 2002, 58, 5779.
32. (b) Konovets, A.; Penciu, A.; Framery, E.; Percina, N.; Goux-Henry, C.; Sinou, D. Tetrahedron Lett. 2005, 46, 3205.
33. Anderson, K. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2005, 44, 6175.
34. Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757.
35. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
36. Paetzold, E.; Kinting, A.; Oehme, G. J. Prakt. Chem. 1987, 329, 725.
37. Goerlich, J. R.; Schmutzler, R. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 702, 211.
38. Wolf, C.; Lerebours, R. Org. Biomol. Chem. 2004, 2, 2161.
39. Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2006, 71, 9499.
40. Collins, C. J.; Hanack, M.; Stutz, H.; Auchter, G.; Schoberth, W. J. Org. Chem. 1983, 48, 5260.
41. Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Tetrahedron 2006, 62, 7521.