General and efficient catalytic amination of aryl chlorides using a palladium/bulky nucleophilic carbene system

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1307-1309

  Huang, Jinkun ^a   Grasa, Gabriella ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001152076     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990987d     Document Type: Article

References (55)

1. (a) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson. G., Stone, F. G., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp 799-938.
2. (b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
3. (c) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
4. (d) Tsuji, J. Synthesis 1990, 739-749.
5. For important recent review of palladium- and nickel-mediated aryl aminations, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
6. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
7. (c) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067.
8. (d) Hartwig, J. F. Synlett 1997, 329-340.
9. (e) Yang, B. H.; Buckwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
10. For representative examples dealing with the amination of aryl chlorides, see: (a) Wolfe, J. P.; Buckwald, S. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 2413-2416.
11. (b) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinburg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840-1853.
12. (c) Bei, X.; Guram, A. S.; Turner, H. W.; Weinburg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
13. (d) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
14. (e) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
15. (f) Brenner, E.; Fort, Y. Tetrahedron Lett. 1998, 39, 5359-5362.
16. (g) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370.
17. (h) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058.
18. (i) Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301-309.
19. (j) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810.
20. For more examples dealing with couplings involving aryl chlorides, see: (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. Engl. 1999, 38, 2411-2413.
21. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. Engl. 1998, 37, 3387-3388.
22. (c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem. Int. Ed. Engl. 1998, 37, 481-483.
23. (d) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10-11.
24. (e) Bei, X.; Guram, A. S.; Turner, H. W.; Weinburg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
25. (f) Indolese, A. F. Tetrahedron Lett 1997, 38, 3513-3516.
26. (g) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024-8030.
27. (h) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993-2996.
28. (a) Regitz, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 725-728.
29. (b) Arduengo, A. J. III; Krafczyk, R. Chem. Zeit. 1998, 32, 6-14.
30. (c) Herrmann, W. A.; Köcher, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2163-2187.
31. Applications of phosphine ligands in homogeneous catalysis: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles andApplications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
32. (b) Parshall, G. W.; Ittel, S. Homogeneous Catalysis; J. Wiley and Sons, New York, 1992.
33. (c) Pignolet, L. H., Ed. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
34. (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 2490-2493.
35. (b) Scholl, M.; Trnka, T. M.; Morgan, J. T.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
36. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
37. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
38. Voges, M. H.; Rømming, C.; Tilset, M. Organometallics 1999, 18, 529-533.
39. Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93-96.
40. (a) Herrmann, W. A.; Elison, M.; Fisher, J.; Köcher, C.; Autus, G. R. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2373.
41. (b) Herrmann, W. A.; Fischer, J.; Elison, M.; Köcher, C.; Autus, G. R. J. Chem. Eur. J. 1996, 2, 772-780.
42. (c) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165-178.
43. Herrmann, W. A.; Goossen, L. T.; Köcher, C.; Autus, G. R. J. Angew. Chem. Int. Ed. Eng. 1996, 35, 2805-2807.
44. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805.
45. (b) Huang, J.; Grasa, G.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Manuscript in preparation.
46. Huang, J.; Nolan, S. P. J. Am. Chem. Soc. In press.
47. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
48. (b) Cornils, B., Herrmann, W. A., Eds. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, 1996.
49. (a) Chem. Eng. News 1998, June 1, 24.
50. (b) Chem. Eng. News 1998, July 13, 71.
51. A recent report by Hartwig shows that a bulky monodentate tertiary phosphine can be used as ancillary ligand in aryl amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
52. (a) Arduengo, A. J., III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
53. (b) Arduengo, A. J., III; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. J. J. Am. Chem. Soc. 1992, 114, 4391-4393.
54. Jafarpour, L.; Stevens, E. D.; Nolan, S. P. Manuscript in preparation.
55. We have recently determined that 1 equiv of the IPr-HCl salt could be used instead of two, leading to similar isolated yields in approximately half the time. A full report of this improvement is forthcoming.