Palladium-Catalyzed Aromatic Animations with in Situ Generated Aminostannanes

Journal of the American Chemical Society

Volumn 116, Issue 17, 1994, Pages 7901-7902

  Guram, Anil S ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33747073729     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00096a059     Document Type: Article

References (19)

1. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992. For recent reports on nucleophilic aromatic substitution reactions of N-nucleophiles with activated aromatic substrates, see:
2. Hattori, T.; Sakamoto, J.; Hayashizaka, N.; Miyano, S. Synthesis 1994, 199.
3. Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1395.
4. Abd-El-Aziz, A.S.; Lee, C. C.; Piorko, A.; Sutherland, R.G. J. Organomet. Chem. 1988, 348, 95. For synthesis of arylamines via Cu-mediated Ullmann condensation, see:
5. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496 and references therein.
6. Tidwell, J. H.; Buchwald, S. L. J. Org. Chem. 1992, 57, 6380.
7. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
8. Related research was recently described while this work was in progress: Hartwig, J. F.; Patt, J.; Paul, F.; Driver, M. S. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; INOR 235.
9. 4 have been described: Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782.
10. Leading references: (a) Jones, K.; Lappert, M. F. Organomet. Chem. Rev. 1966, 1, 67 and references therein
11. Chandra, G.; George, T. A.; Lappert, M. F. J. Chem. Soc. C 1969, 2565 and references therein.
12. In contrast, thiostannanes are very robust and have been more generally employed in related Pd-catalyzed reactions; see: (a) Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621.
13. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657.
14. 2. Studies to elucidate the reduction mechanism are currently underway.
15. This transamination reaction was originally reported by Jones and Lappert. Secondary amines and primary aromatic amines (e.g., aniline and derivatives) form aminostannanes, whereas primary aliphatic amines form aminodistannanes; see: Jones, K.; Lappert, M. F. J. Chem. Soc. 1965, 1944.
16. For a general review on transition metal catalyzed coupling reactions, see: Tamao, K. Comprehensive Organic Synthesis; Trost,B. M.,Ed.;Pergamon Press, Inc., New York, 1991; Vol. 3, p 435.
17. Complexes containing a Pd-N bond are rare and presumably decompose via β-hydride elimination: (a) Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem, Soc. 1983, 105, 5002.
18. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
19. Paul, F.; PaH, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.