Reductive carbodiazenylation of nonactivated olefins via aryl diazonium salts

Organic Letters

Volumn 8, Issue 15, 2006, Pages 3323-3325

  Heinrich, Markus R ^a   Blank, Olga ^a   Wölfel, Sabrina ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746877486     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0611393     Document Type: Article

References (30)

1. (a) Nakhla, J. S.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 2893-2901.
2. (b) Ney, J. E.; Hay, M. B.; Yang, Q.; Wolfe, J. P. Adv. Synth. Catal. 2005, 347, 1614-1620.
3. (c) Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575-2578.
4. Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024-15025.
5. Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230-3233.
6. Ruck, R. T.; Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. Angew. Chem., Int. Ed. 2004, 43, 5372-5374.
7. Basuli, F.; Aneetha, H.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2005, 127, 17992-17993.
8. (a) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2000, 122, 6496-6497.
9. (b) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717-4727.
10. (c) Panchaud, P.; Renaud, P. J. Org. Chem. 2004, 69, 3205-3207.
11. (d) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas, S. J. Org. Chem. 2004, 69, 2755-2759.
12. (e) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2005, 7, 2587-2590.
13. (f) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2002, 4, 4257-4260.
14. Barton, D. H. R.; Jaszberenyi, J. C.; Theodorakis, E. A.; Reibenspies, J. H. J. Am. Chem. Soc. 1993, 115, 8050-8059.
15. Girard, P.; Guillot, N.; Motherwell, W. B.; Potier, P. Chem. Commun. 1995, 2385-2386.
16. (a) Citterio, A.; Minisci, F.; Albinati, A.; Bruckner, S. Tetrahedron Lett. 1980, 21, 2909-2910.
17. (b) Citterio, A.; Minisci, F.; Vismara, E. J. Org. Chem. 1982, 47, 81-88.
18. (c) Minisci, F.; Coppa, F.; Fontana, F.; Pianese, G.; Zhao, L. J. Org. Chem. 1992, 57, 3929-3933.
19. (a) Rondestvedt, C. S. Org. React. 1976, 24, 225-259.
20. (b) Citterio, A.; Vismara, E. Synthesis 1980, 291-292.
21. (a) Al Adel, I.; Salami, B. A.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930-933.
22. (b) Al Adel, I.; Salami, B. A.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 934-938.
23. For details, see the Supporting Information
24. Galli, C. Chem. Rev. 1988, 88, 765-792.
25. (a) Citterio, A.; Ramperti, M.; Vismara, E. J. Heterocycl. Chem. 1981, 18, 763-766.
26. (b) Citterio, A.; Minisci, F. J. Org. Chem. 1982, 47, 1759-1761.
27. Azo compound 4e was chosen for more convenient isolation of the carboamination product 13.
28. For hydrogenations of azo compounds, see: (a) Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Synth. Commun. 2005, 35, 1161-1165.
29. (b) Martin, V. V.; Rothe, A.; Gee, K. R. Bioorg. Med. Chem. Lett. 2005, 15, 1851-1855.
30. (c) Alonso-Alija, C.; Michels, M.; Peilstöcker, K.; Schirok, H. Tetrahedron Lett. 2004, 45, 95-98.