The novel insertion of imines into a late-metal-carbon σ-bond: Developing a palladium-mediated route to polypeptides

Organometallics

Volumn 17, Issue 1, 1998, Pages 4-6

  Dghaym, Rania D ^a   Yaccato, Karin J ^a   Arndtsen, Brace A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002789134     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9709244     Document Type: Article

References (28)

1. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
2. For a recent review, see: Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
3. Johnson, J. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267.
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7. Obora, Y.; Ohta, T.; Stem, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745.
8. Products consistent with imine insertion into a M-COR bond have been suggested in several systems; however, the imine insertion step into the metal-acyl is only postulated: (a) Alper, H.; Amaratunga, S. J. Org. Chem. 1982, 47, 3595. (b) Reduto, A. C.; Hegedus, L. S. Organometallics 1995, 14, 1586. (c) Muller, F.; van Koten, G.; Vrieze, K.; Heijdenrijk, D. Organometallics 1989, 8, 33.
9. Products consistent with imine insertion into a M-COR bond have been suggested in several systems; however, the imine insertion step into the metal-acyl is only postulated: (a) Alper, H.; Amaratunga, S. J. Org. Chem. 1982, 47, 3595. (b) Reduto, A. C.; Hegedus, L. S. Organometallics 1995, 14, 1586. (c) Muller, F.; van Koten, G.; Vrieze, K.; Heijdenrijk, D. Organometallics 1989, 8, 33.
10. Products consistent with imine insertion into a M-COR bond have been suggested in several systems; however, the imine insertion step into the metal-acyl is only postulated: (a) Alper, H.; Amaratunga, S. J. Org. Chem. 1982, 47, 3595. (b) Reduto, A. C.; Hegedus, L. S. Organometallics 1995, 14, 1586. (c) Muller, F.; van Koten, G.; Vrieze, K.; Heijdenrijk, D. Organometallics 1989, 8, 33.
11. Imine insertions into M-H bonds are known and have been postulated in catalytic hydrogenations: (a) Fryzuk, M. O.; Piers, W. E. Organometallics 1990, 9, 986. (b) Debad, J. D.; Legzdins, P.; Lumb, S. A.; Batchelor, R. J.; Einstein, F. W. B. Organometallics 1995, 14, 2543. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703 and references therein.
12. Imine insertions into M-H bonds are known and have been postulated in catalytic hydrogenations: (a) Fryzuk, M. O.; Piers, W. E. Organometallics 1990, 9, 986. (b) Debad, J. D.; Legzdins, P.; Lumb, S. A.; Batchelor, R. J.; Einstein, F. W. B. Organometallics 1995, 14, 2543. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703 and references therein.
13. Imine insertions into M-H bonds are known and have been postulated in catalytic hydrogenations: (a) Fryzuk, M. O.; Piers, W. E. Organometallics 1990, 9, 986. (b) Debad, J. D.; Legzdins, P.; Lumb, S. A.; Batchelor, R. J.; Einstein, F. W. B. Organometallics 1995, 14, 2543. (c) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703 and references therein.
14. Polypeptide syntheses: Bayer, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 113.
15. Rülke, R. E.; Delis, J. G. P.; Groot, A. M.; Elsevier: C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Goubitz, K.; Schenk, H. J. Organomet. Chem. 1996, 422, 109.
16. The spectroscopic and elemental analysis data for 3a-d, 5a-d, and 6a-c are provided in the Supporting Information.
17. Knight, D. A.; Dewey, M. A.; Stark, G. A.; Bennet, B. K.; Arif, A. M.; Gladysz, B. K. Organometallics 1993, 12, 4523.
18. Mononuclear complexes with side-on π-bound imines have only been reported with strong back-bonding early metals: (a) Durfee, L. D.; Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 75. (b) Buchwald, S. L.; Watson, R. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486.
19. Mononuclear complexes with side-on π-bound imines have only been reported with strong back-bonding early metals: (a) Durfee, L. D.; Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1990, 9, 75. (b) Buchwald, S. L.; Watson, R. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486.
20. Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664.
21. Bryndza, H. E.; Tam, W. Chem. Rev. (Washington, D.C.) 1988, 88, 1163.
22. 16b
23. (a) Sandorfy, C. The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Wiley: New York, 1970; p 1.
24. (b) Wiberg, K. B.; Nakaji, D. Y.; Morgan, K. M. J. Am. Chem. Soc. 1993, 115, 3527.
25. 15
26. w) = 0.0717 (0.1330), GOF = 0.991, T = 293 K. Full details of the crystallographic analysis of 6b are described in the Supporting Information.
27. Markies, B. A.; Rietveld, M. H. P.; Boersma, J.; Spek, A. L.; van Koten G. J. Organomet. Chem. 1992, 424, C12. van Asselt, R.; Gielens E. E. C. G.; Rulke, R. E.; Vrieze, K.; Elsevier: C. J. J. Am. Chem. Soc. 1994, 116, 977.
28. Markies, B. A.; Rietveld, M. H. P.; Boersma, J.; Spek, A. L.; van Koten G. J. Organomet. Chem. 1992, 424, C12. van Asselt, R.; Gielens E. E. C. G.; Rulke, R. E.; Vrieze, K.; Elsevier: C. J. J. Am. Chem. Soc. 1994, 116, 977.