Convenient Synthesis of Alkylhydrazides by the Cobalt-Catalyzed Hydrohydrazination Reaction of Olefins and Azodicarboxylates

Journal of the American Chemical Society

Volumn 126, Issue 18, 2004, Pages 5676-5677

  Waser, Jérôme ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; AZODICARBOXYLATE; COBALT COMPLEX; COBALT HYDRIDE; DICARBOXYLIC ACID; HYDRAZINE DERIVATIVE; OXYGEN; SILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; HYDROHYDRAZINATION REACTION; OXYGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 2442590635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048698u     Document Type: Article

References (21)

1. Brown, B. R. The Organic Chemistry of Aliphatic Nitrogen Compounds; Oxford University: New York, 1994.
2. (a) Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205.
3. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
4. (c) Ricci, A. Modern Amination Methods; Wiley-VCH: Weinheim, 2000.
5. (d) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395.
6. (e) Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397.
7. (f) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
8. (g) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
9. (h) Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5261.
10. (i) Baran, P. S.; Guerrero, C. A.; Corey, E. J. Org. Lett. 2003, 5, 1999.
11. (a) Kato, K.; Yamada, T.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 179.
12. (b) Isayama, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1990, 63, 1305.
13. (c) Tokuyasu, T.; Kunikawa, S.; Musuyama, A.; Nojima, M. Org. Lett. 2002, 4, 3595.
14. (d) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 6, 1071.
15. (e) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 4, 573.
16. modp = 1-morpholinocarbamoyl-4,4-dimethyl-1,3-pentanedionato; dpm = dipivaloylmethanato.
17. Tada, M. Rev. Heteroat. Chem. 1999, 20, 97.
18. Punnyamurthy, T.; Bhatia, B.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. Tetrahedron 1997, 53, 7649.
19. Burrows, R. C.; Bailar, J. C. J. Am. Chem. Soc. 1966, 88, 4150.
20. The regioselectivity of the hydrocobaltation step has been studied, see. for example: Derenne, S.; Gaudemer, A.; Johnson, M. D. J. Organomet. Chem. 1987, 322, 229. The chief differences observed between the various Co-complexes prepared from 5-8 arise from the competitive reduction of the azodicarboxylate versus hydrocobaltation. We hypothesize that the steric bulk associated with di-tert-butyl azodicarboxylate (3) is critical in minimizing its reduction. The effect of the ligands in this respect is not clear and is the subject of ongoing investigations.
21. Verdaguer, X.; Lange, U. E. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 1998, 37, 1103.