Bulky alkylphosphines with neopentyl substituents as ligands in the amination of aryl bromides and chlorides

Journal of Organic Chemistry

Volumn 71, Issue 14, 2006, Pages 5117-5125

  Hill, Lensey L ^a   Moore, Lucas R ^a   Huang, Rongeai ^a   Craciun, Raluca ^a   Vincent, Andrew J ^a   Dixon, David A ^a   Chou, Joe ^b   Woltermann, Christopher J ^b   Shaughnessy, Kevin H ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b FMC CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLPHOSPHINES; HARTWIG-BUCHWALD AMINATION; NEOPENTYL SUBSTITUENTS; TRI(TERT-BUTYL)PHOSPHINE (TTBP);

BROMINE COMPOUNDS; CATALYSTS; CHLORIDE MINERALS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS;

AMINATION;

BROMIDE; CHLORIDE; DI (TERT BUTYL)NEOPENTYLPHOSPHINE; LIGAND; PALLADIUM; PENTANE; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRI (TERT BUTYL)PHOSPHINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CALCULATION; CATALYSIS; CATALYST; ELECTRON TRANSPORT; GEOMETRY; HIGH TEMPERATURE; LIGAND BINDING; MOLECULAR SIZE;

AMINATION; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; STEREOISOMERISM; TIME FACTORS;

EID: 33745714398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060303x     Document Type: Article

References (55)

1. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
2. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
3. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
4. Prim, D.; Campagne, J.-M.; Jospeph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
5. Blaser, H.-U.; Indolese, A. F.; Naud, F.; Nettekoven, U.; Schnyder, A. Adv. Synth. Catal. 2004, 346, 1583-1598.
6. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
7. Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479-6486.
8. Stauffer, S. R.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 6977-6985.
9. Stauffer, S. R.; Steinbeiser, M. A. Tetrahedron Lett. 2005, 46, 2571-2575.
10. Lee, D.-Y.; Hartwig, J. F. Org. Lett. 2005, 7, 1169-1172.
11. Ehrentraut, A.; Zapf, A.; Beller, M. J. Mol. Catal A: Chem. 2002, 182-183, 515-523.
12. Tewari, A.; Hein, M.; Zapf, A.; Beller, M. Tetrahedron 2005, 61, 9705-9709.
13. Li, G. Y.; Zeng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681.
14. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
15. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
16. Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820-3827.
17. Huang, X.; Andersen, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
18. Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413-2415.
19. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
20. Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
21. Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Reiermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem.-Eur. J. 2004, 10, 2983-2990.
22. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. J. Org. Chem. 2003, 68, 452-459.
23. Urgaonkar, S., Verkade, J. G. J. Org. Chem. 2004, 69, 9135-9142.
24. Venkat Reddy, Ch.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2005, 7, 4427-4430.
25. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
26. Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729-7737.
27. Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
28. Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482.
29. Arentsen, K.; Caddick, S.; Cloke, F. G. N. Tetrahedron 2005, 61, 9710-9715.
30. Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944-6945.
31. Alcazar-Roman, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 12905-12906.
32. DeVasher, R. B.; Spruell, J. M.; Dixon, D. A.; Broker, G. A.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H. Organometallics 2005, 24, 962-971.
33. FMC, Lithium Division is currently scaling up production of DTBNpP.
34. Mason, R.; Textor, M.; Al-Salem. N.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1976, 292-293.
35. King, R. B.; Cloyd, J. C., Jr.; Reimann, R. H. J. Org. Chem. 1976, 41, 972-977.
36. King, R. B.; Cloyd, J. C., Jr.; Norins, M. E.; Reimann, R. H. J. Coord. Chem. 1977, 7, 23-26.
37. Dahlenburg, L.; Yardimcioglu, A. J. Organomet. Chem. 1985, 291, 371-386.
38. Dahlenburg, L.; Höck, N. Inorg. Chim. Acta 1985, 104, L29-L30.
39. Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2001, 66, 9067-9070.
40. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
41. Bartik, T.; Himmler, T.; Schulte, H. G.; Seevogel, K. J. Organomet. Chem. 1984, 272, 29-41.
42. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
43. Vastag, S.; Heil, B.; Marko, L. J. Mol. Catal. 1979, 5, 189-195.
44. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630-6636.
45. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
46. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
47. Küchle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994, 100, 7535-7542 and references therein; http://www.theochem.unistuttgart.de/ pseudopotentials/.
48. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
49. Slater, J. C. Phys. Rev. 1951, 81, 385.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
51. Lee, C.; Yang, W.; Parry, R. G. Phys. Rev. B 1988, 37, 785-789.
52. Taverner, B. C. J. Comput. Chem. 1996, 17, 1612-1623.
53. Taverner, B. C. STERIC, 1.11, 1995; http://www.ccl.net/cca/software/ SOURCES/C/steric/index.shtml.
54. Garza, J.; Vargas, R.; Nichols, J. A.; Dixon, D. A. J. Chem. Phys. 2001, 114, 639-651.
55. Zhan, C.-G.; Nichols, J. A.; Dixon, D. A. J. Phys. Chem. A 2003, 107, 4184-4195.