Catalysis with platinum-group alkylamido complexes. The active palladium amide in catalytic aryl halide aminations as deduced from kinetic data and independent generation

Organometallics

Volumn 15, Issue 12, 1996, Pages 2794-2805

  Louie, Janis ^a   Paul, Frédéric ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5844307923     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960188o     Document Type: Article

References (59)

1. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987.
2. One reaction of this type is the hydroamination of alkenes and alkynes. For leading references see the following nine citations:
3. Catalysis with a low valent arylamido complex has been reported, although turnover numbers are not high: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744 and references therein.
4. Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
5. Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
6. Brunet, J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221.
7. Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917-1926.
8. Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
9. Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
10. Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
11. McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
12. Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163-1188.
13. Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1-40.
14. Examples of a nickel dimethylamido complex were prepared over 20 years ago: Klein, H. F.; Karsch, H. H. Chem. Ber. 1973, 106, 2438-2454.
15. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
16. Rahim, M.; Bushweller, C. H.; Ahmed, K. J. Organometallics 1994, 13, 4952-4958.
17. Michelman, R. I.; Ball, G. E.; Bergman, R. G.; Andersen, R. A. Organometallics 1994, 13, 869-881.
18. Sarneski, J. E.; McPhail, A. T.; Onan, K. D.; Erickson, L. E.; Reilley, C. N. J. Am. Chem. Soc. 1977, 99, 7376-7378.
19. A dimeric alkyl, benzyl amide has been prepared: Fryzuk, M. D.; Piers, W. E. Organometallics 1990, 9, 986-98.
20. Kosugi, M.; Kameyama, M.; Sano, H.; Migita, T.Nippon Kagaku Kaishi 1985, 3, 547-551.
21. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
22. Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
23. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
24. The two following references report aryl halide amination methods methods without tin reagents.
25. A tin free system has also been developed. Louie, J.; Hartwig, J. P. Tetrahedron Lett. 1995, 36, 3609.
26. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
27. Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780.
28. Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
29. Lindley, J. Tetrahedron 1984, 40, 1433-1456.
30. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496-1502.
31. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
32. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
33. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
34. A recent review of these data is the following: Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031.
35. Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; W., T.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805-4814.
36. 1H NMR spectra were different from the amine complex, ruling out formation of 3 by an amine impurity in the tin amide.
37. Segel, I. H. In Enzyme Kinetics; John Wiley and Sons, Inc.: New York, 1975; pp 113-118.
38. Buchwald and Guram reported a 2:1 selectivity for formation of N,N-dimethylanilines over N,N-diethylanilines as a competition study. Their reactions were run in the presence of 1.4 equiv of both the diethyl- and dimethylamido tin reagents per equivalent of aryl bromide. In order to obtain the accurate value that our comparison requires, a constant concentration of the two tin amides must be ensured. With the 10-fold excess of each tin amide in our experiments, a 3:1 selectivity was observed.
39. Park, S.; Roundhill, D. M.; Rheingold, A. L. Inorg. Chem. 1987, 26, 3972-3974.
40. Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615-623.
41. Joslin, F. L.; Johnson, M. P.; Mague, J. T.; Roundhill, D. M. Organometallics 1991, 10, 2781-2794.
42. A variety of biaryls are formed under these conditions, presumably by exchange of palladium- and phosphorus-bound aryl groups similar to that in the following four leading references.
43. Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
44. Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
45. Wallow, T. I.; Novak, B. M. J. Og. Chem. 1994, 59, 5034.
46. Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
47. March, J. Advanced Organic Chemistry; 3rd ed.; John Wiley and Sons: New York, 1985.
48. Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412.
49. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
50. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
51. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
52. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
53. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
54. Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276-2282.
55. Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626.
56. Imine hydrogenation catalyzed by rhodium and iridium complexes would be expected to occur through an amide complex. However, mechanistic data is scarce. A direct observation of imine insertion that produces an amide complex potentially similar to those in catalytic systems is the following: Fryzuk, M. D.; Piers, W. E. Organometallics 1990, 9, 986-98.
57. Halpern, J. Inorg. Chem. Acta 1981, 50, 11.
58. Ziegler, C. B., Jr.; Heck, R. F. J. Org. Chem. 1978, 43, 2941-2946.
59. Jones, K.; Lappert, M. F. J. Chem. Soc. 1965, 1944-1951.