Synthesis, structure, and reactivity of a palladium hydrazonato complex: A new type of reductive elimination reaction to form C-N bonds and catalytic arylation of benzophenone hydrazone

Angewandte Chemie - International Edition

Volumn 37, Issue 15, 1998, Pages 2090-2093

  Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Aminations; Arylations; Cross coupling; Hydrazones; Palladium

Indexed keywords

EID: 0032541291     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980817)37:15<2090::AID-ANIE2090>3.0.CO;2-A     Document Type: Article

References (28)

1. M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 7217-7218.
2. M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 8232-8245.
3. K. Koo, G. L. Hillhouse, Organometallics 1995, 14, 4421-4423.
4. L. A. Villanueva, K. A. Abboud, J. M. Boncella, Organometallics 1994, 13, 3921-3931.
5. Review: J. F. Hartwig, Synlett 1996, 329-340; J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067.
6. Review: J. F. Hartwig, Synlett 1996, 329-340; J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067.
7. Review: J. F. Hartwig, Synlett 1996, 329-340; J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067.
8. J. Louie, J. F. Hartwig, Tetrahedron Lett. 1995, 36, 3609-3612.
9. A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456-1459; Angew. Chem. Int. Ed. Engl. 1995, 34, 1348-1350.
10. A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456-1459; Angew. Chem. Int. Ed. Engl. 1995, 34, 1348-1350.
11. J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215-7216.
12. For a structurally characterized example, see K. Burgess, B. F. G. Johnson, J. Lewis, P. R. Raithby, J. Chem. Soc. Dalton Trans. 1982. 263-269.
13. S. Gambarotta, M. Basso-Bert, C. Floriani, C. Gaustini, J. Chem. Soc. Chem. Commun. 1982, 374-375.
14. S. Gambarotta, C. Floriani, A. Chiesi-Villa, C. Guastini, Inorg. Chem. 1983, 22, 2029-2034.
15. -1.
16. -1 (in ω), (1.26 + 0.3tanθ)°, - 105°C, 8616 reflections with 8231 unique. The data were corrected for Lorentz and polarization factors. No absorption correction was applied. The structure was solved by direct methods and refined with Fourier techniques and teXan software. Number of observations (I> 3.00σ(I)) 3147 and number of variables 577. H atoms were included but not refined. R = 0.056, wR = 0.64, refined against |F|. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-101 249. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
17. P. A. S. Smith, Derivatives of Hydrazone and other Hydronitrogens Having N-N Bonds, Benjamin, Reading, MA, 1983, p. 46.
18. M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1996, 108, 4206-4207.
19. G. Mann, J. Hartwig, J. Am. Chem. Soc. 1996, 118, 13109-13110.
20. M. S. Driver, J. F. Hartwig, Organometallics 1997, 16, 5706-5715.
21. This complex was prepared in similar fashion to the p-tBu analogue.
22. G. Mann, M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 827-828.
23. A recent synopsis of these mechanisms and their accompanying data is included in C. Amatore, F. Pfluger, Organometallics 1990, 9, 2276-2282.
24. J. P. Wolfe, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6359-6362.
25. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, in press.
26. J. March, Advanced Organic Chemistry, 3rd ed., Wiley, New York, 1985.
27. M. Busch, S. Schäffner, Chem. Ber. 1923, 56, 1612-1616.
28. Note added in proof (July 22, 1998). Buchwald et al. have recently reported a variety of indoles prepared by the hydrazone arylation strategy. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 6621-6622.