Oxidative addition of α-bromoglycine to palladium(0) and platinum(0) complexes: α-metallated amino acids as models for intermediates in the metal-catalyzed hydrogenation of dehydroamino acids

European Journal of Inorganic Chemistry

Volumn , Issue 3, 1998, Pages 375-379

  Kayser, Bernd ^a   Missling, Christopher ^a   Knizek, Jörg ^a   Nöth, Heinrich ^a   Beck, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Oxidative addition; Palladium; Platinum; Bromoglycinate; Metallated amino acids

Indexed keywords

AMINO ACIDS; ANTIMONY COMPOUNDS; FLUORINE COMPOUNDS; HYDROGENATION; PALLADIUM COMPOUNDS; PLATINUM; PLATINUM COMPOUNDS; SILVER COMPOUNDS; X RAY DIFFRACTION;

AMINO-ACIDS; BIPYRIDYL; CATIONICS; DEHYDROAMINO ACID; DIBENZYLIDENEACETONE; METAL-CATALYZED; OXIDATIVE ADDITIONS; PLATINUM(0) COMPLEXES; Α-BROMOGLYCINATE; Α-METALLATED AMINO ACID;

PALLADIUM;

EID: 0002601854     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0682(199803)1998:3<375::AID-EJIC375>3.0.CO;2-9     Document Type: Article

References (49)

1. K. Severin, R. Bergs, W. Beck, Angew. Chem., in press.
2. X-ray diffraction measurements.
3. [3a] R. Kober, W. Steglich, Liebigs Ann. Chem. 1983, 599-609.
4. [3b] R. Kober, K. Papadopoulos, W. Miltz, D. Enders, W. Steglich, Tetrahedron 1985, 41, 1693-1701.
5. [3c] P. Münster, W. Steglich, Synthesis 1987, 223-225.
6. [3d] G. Apitz, M. Jäger, S. Jaroch, S. Kratzel, L. Schäffeler, W. Steglich, Tetrahedron 1993, 49, 8223-8232.
7. [3e] Th. Bretschneider, W. Miltz, P. Münster, W. Steglich, Tetrahedron 1988, 44, 5403-5414.
8. [3f] V. A. Buraess, C. J. Easton, M. P. Hay, P. J. Steel, Aust. J Chem. 1988, 41, 701-710.
9. [3g] S. Jaroch, T. Schwarz, W. Steglich, P. Zistier, Angew Chem. 1993, 105, 1803-1805; Angew. Chem. Int. Ed Engl. 1993, 32, 1771.
10. [3g] S. Jaroch, T. Schwarz, W. Steglich, P. Zistier, Angew Chem. 1993, 105, 1803-1805; Angew. Chem. Int. Ed Engl. 1993, 32, 1771.
11. [4a] B. Kayser, K. Polborn, W. Steglich. W. Beck, Chem. Ber. 1997, 130, 171-177.
12. [4b] B. Kayser, H. Nöth, M. Schmidt, W. Steglich, W. Beck, Chem. Ber. 1996, 129, 1617-1620.
13. [5a] G. Jaouen, A. Vessiéres, I. S. Butler, Ace. Chem. Res. 1993, 26, 361-369.
14. [5b] M. Salmain, M. Gunn, A. Gorfti, S. Top, G. Jaouen, Bioconjugate Chem. 1993, 4, 425-433.
15. [5c] A. Gorfti, M. Salmain, G. Jaouen, M. J. McGlinchey, A. Bennouna, A. Mousser, Organometallics 1996, 15, 142-151.
16. [5d] A. J. Gleichmann, J. M. Wolff, W. S. Sheldrick, J. Chem. Soc., Dalton Trans. 1995, 1549-1554.
17. [5e] J. M. Wolff, A. J. Gleiehmann, W. S. Sheldrick, J. Inorg. Biochem. 1995, 59, 219.
18. [5f] J. M. Wolff, W. S. Sheldrick, Chem. Ber. 1997, 130, 981-988; J. Organomet. Chem. 1997, 531, 141-149.
19. [5f] J. M. Wolff, W. S. Sheldrick, Chem. Ber. 1997, 130, 981-988; J. Organomet. Chem. 1997, 531, 141-149.
20. [5j] R. Krämer. Angew. Chem. 1996, 108, 1287-1289; Angew. Chem. Int. Ed Engl. 1996, 35, 1197-1199.
21. [5j] R. Krämer. Angew. Chem. 1996, 108, 1287-1289; Angew. Chem. Int. Ed Engl. 1996, 35, 1197-1199.
22. [5h] M. Schweiger, T. Ederer, K. Sünkel, W. Beck, J. Organomet. Chem., in press.
23. [6a] A. S. C. Chan, J. J. Pluth, J. Halpern, Inorg. Chim. Acta 1979, 37, L477-L479.
24. [6b] A. S. C. Chan, J. Halpern, J. Am. Chem. Soc. 1980, 702, 838-840.
25. [6c] J. Halpern, Pure Appl. Chem. 1983, 55, 99-196.
26. [7a] J. M. Brown, P. A. Chaloner, J. Chem. Soc., Chem. Commun. 1980, 344-346.
27. [7b] J. M. Brown, P. J. Maddox, J. Chem. Soc. Chem. Commun 1987, 1276-1278.
28. [7c] J. M. Brown, Chem. Soc. Rev. 1993, 22, 25-41.
29. [7d] J. A. Ramsden, T. D. W. Claridge, J. M. Brown, J. Chem. Soc. Chem. Commun. 1995, 2469-2471.
30. [8a] D. Mani, H.-T. Schacht, A. Powell, H. Vahrenkamp, Organometallics 1987, 6, 1360-1361.
31. [8b] D. Mani, H.-T. Schacht, A. K Powell, H. Vahrenkamp, Chem. Ber. 1989, 122, 2245-2251.
32. J. A. Wiles, S. H. Bergens, J. Am. Chem. Soc. 1997, 119, 2940-2941.
33. A. J. Canty, G. K. Anderson, in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, 1995, 9, 225, 431.
34. J. P. Birk, J. Halpern, A. L. Pickard, J. Am. Chem. Soc. 1968, 90, 4491-4492; A. R. Siedle, R. A. Newmark, W. B. Gleason, J. Am Chem. Soc. 1986, 108, 767-773.
35. J. P. Birk, J. Halpern, A. L. Pickard, J. Am. Chem. Soc. 1968, 90, 4491-4492; A. R. Siedle, R. A. Newmark, W. B. Gleason, J. Am Chem. Soc. 1986, 108, 767-773.
36. B. A. Markies, A. J. Canty, W. de Graaf, J. Boersma, M. D. Janssen, M. P Hogerheide, W. J. J. Smeets, A. L. Spek, G. van Koten, J. Organomet. Chem. 1994, 482, 191-199; P. K. Byers, A. J. Canty, Organometallics 1990, 9, 210-220.
37. B. A. Markies, A. J. Canty, W. de Graaf, J. Boersma, M. D. Janssen, M. P Hogerheide, W. J. J. Smeets, A. L. Spek, G. van Koten, J. Organomet. Chem. 1994, 482, 191-199; P. K. Byers, A. J. Canty, Organometallics 1990, 9, 210-220.
38. W. Henderson, R. D. W. Kemmitt, A. L. Davis, J. Chem. Soc., Dalton Trans. 1993, 2247-2250.
39. R. van Asselt, E. E. C. G. Gielens, R. E. Rülke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc. 1994, 116, 977-985; J. G. P. Delis, P. G. Aubel, K. Vrieze, P. W. N. M. van Leeuwen, Organometallics 1997, 16, 2948-2957; R. E. Rulke, D. Kliphuis, C. J. Elsevier, J. Fraanje, K. Goubitz, P. W. N. M. van Leeuwen, K. Vrieze, J. Chem. Soc., Chem. Commun 1994, 1817-1819.
40. R. van Asselt, E. E. C. G. Gielens, R. E. Rülke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc. 1994, 116, 977-985; J. G. P. Delis, P. G. Aubel, K. Vrieze, P. W. N. M. van Leeuwen, Organometallics 1997, 16, 2948-2957; R. E. Rulke, D. Kliphuis, C. J. Elsevier, J. Fraanje, K. Goubitz, P. W. N. M. van Leeuwen, K. Vrieze, J. Chem. Soc., Chem. Commun 1994, 1817-1819.
41. R. van Asselt, E. E. C. G. Gielens, R. E. Rülke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc. 1994, 116, 977-985; J. G. P. Delis, P. G. Aubel, K. Vrieze, P. W. N. M. van Leeuwen, Organometallics 1997, 16, 2948-2957; R. E. Rulke, D. Kliphuis, C. J. Elsevier, J. Fraanje, K. Goubitz, P. W. N. M. van Leeuwen, K. Vrieze, J. Chem. Soc., Chem. Commun 1994, 1817-1819.
42. P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, J. Organomet Chem. 1987, 336, C55-C60; V. De Felice, V. G. Albano, C. Castellari, M. E. Cucciolito, A. De Renzi, J. Organomet. Chem 1991, 403, 269-277; B. A. Markies, M. H. P. Rietveld, J. Boersma, A. L. Spek, G. van Koten, J. Organomet. Chem. 1992, 424, C12-C16.
43. P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, J. Organomet Chem. 1987, 336, C55-C60; V. De Felice, V. G. Albano, C. Castellari, M. E. Cucciolito, A. De Renzi, J. Organomet. Chem 1991, 403, 269-277; B. A. Markies, M. H. P. Rietveld, J. Boersma, A. L. Spek, G. van Koten, J. Organomet. Chem. 1992, 424, C12-C16.
44. P. K. Byers, A. J. Canty, B. W. Skelton, A. H. White, J. Organomet Chem. 1987, 336, C55-C60; V. De Felice, V. G. Albano, C. Castellari, M. E. Cucciolito, A. De Renzi, J. Organomet. Chem 1991, 403, 269-277; B. A. Markies, M. H. P. Rietveld, J. Boersma, A. L. Spek, G. van Koten, J. Organomet. Chem. 1992, 424, C12-C16.
45. I. Zahn, K. Polborn, B. Wagner, W. Beck, Chem. Ber. 1991, 124, 1065-1073; A. G. Thayer, N. C. Payne. Acta Crystallogr., Sect. C 1986, 42, 1305-1310.
46. I. Zahn, K. Polborn, B. Wagner, W. Beck, Chem. Ber. 1991, 124, 1065-1073; A. G. Thayer, N. C. Payne. Acta Crystallogr., Sect. C 1986, 42, 1305-1310.
47. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100822. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambrige CB2 1EZ, U.K. [Fax: (internat.) + 44 (0)1223 336033; e-mail: deposit@ccdc.cam.ac.uk].
48. M. F. Rettig, P. M. Maitlis, Inorg. Synth. 1990, 28, 110-113.
49. U. Nagel, Chem. Ber. 1982, 115, 1998-1999.