Convenient Routes to Vicinal Diamines: Coupling of Nitriles or N-(Trimethylsilyl)imines Promoted by NbCl4(THF)2

Journal of the American Chemical Society

Volumn 109, Issue 10, 1987, Pages 3152-3154

  Roskamp, Eric J ^a   Pedersen, Steven F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000369272     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00244a052     Document Type: Article

References (14)

1. For reviews, see: (a) Block, E. Org. React. 1984, 30, 457. Lai, Y. H. Org. Prep. Procd. Int. 1980, 112, 361. Ho, T. L. Synthesis 1979, 1.
2. McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S. J. Org. Chem. 1976, 41, 260. Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041.
3. McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255.
4. Jung, S. H.; Kohn, H. J. Am. Chem. Soc. 1985, 107, 2931. Natsugari, H.; Whittle, R. R.; Weinreb, S. M. 1984, 106, 7867. Jung, S. H.; Kohn, H. Tetrahedron Lett. 1984, 25, 399. Gideon, L. F.; Pradip, P. J. Org. Chem. 1984, 49, 1314. (e) Becker, P. N.; Bergman, R. G. Organometallics 1983, 2, 787. (f) Sharpless, K. B.; Singer, S. P. J. Org. Chem. 1976, 41, 2504.
5. Imwinkelried, R.; Seebach, D. Helv. Chem. Acta 1984, 67, 1496.
6. For a review of transition metal-imido chemistry, see: Nugent, W. A.; Haymore, B. A. Coord. Chem. Rev. 1980, 31, 123.
7. van Tamelen, E. E.; Akemark, B.; Sharpless, K. B. J. Am. Chem. Soc. 1969, 91, 1552. Sharpless, K. B.; Hanzlik, R. P.; van Tamelen, E. E. 1968, 90, 209. van Tamelen, E. E.; Schwartz, M. 1965, 87, 3277.
8. Manzer, L. E. Inorg. Chem. 1977, 16, 525. for a more convenient synthesis of NbCl4(THF)2, see the supplementary material.
9. Hawn, G. G.; Chang, C. A.; Douglas, B. E. Inorg. Chem. 1979, 18, 1266.
10. Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 9, 539.
11. For example, see: (a) Churchill, M. R.; Wasserman, H. J.; Belmonte, P. A.; Schrock, R. R. Organometallics 1982, 1, 559. Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443 and references therein.
12. Nb2Cl6H2(PMe3)4has been mentioned but no details have been reported: Sattelberger, A. P.; Wilson, R. B., Jr.; Huffman, J. C. Inorg. Chem. 1982, 21, 4179.
13. Liebner, J. E.; Jacobus, J. J. Ore. Chem. 1979, 44, 449.
14. Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6059. Griller, C.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317 and references therein.