Tricarbonyl-η6-[(2-thiophenyl)arene]- and-η6-[(2- thiophenyl)carbonylarene]-chromium complexes: Preparation and conformational study

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2000, Pages 901-905

  Prim, Daimien ^a   Tranchier, Jean Philippe ^a   Rose Munch, Françoise ^a   Rose, Eric ^a   Vaissermann, Jacqueline ^b  

^a CNRS   (France)

^b EUROPEAN SPACE AGENCY   (France)

Author keywords

Arenetricarbonyl chromium complexes; Cross coupling reaction; Palladium; Thiophenes

Indexed keywords

CHEMICAL REACTIONS; CHROMIUM COMPOUNDS; PALLADIUM;

ARENETRICARBONYL CHROMIUM COMPLEX; CHLOROANISOLES; CHROMIUM COMPLEXES; COMPLEX 1; CONDITION; CONFORMATIONAL STUDY; CROSS COUPLING REACTIONS; PALLADIUM-CATALYZED; THIOPHENE DERIVATIVES; THIOPHENYL;

THIOPHENE;

CHROMIUM DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; COMPLEX FORMATION; CONFORMATION; CROSS REACTION; CRYSTAL STRUCTURE; SYNTHESIS;

EID: 0034071566     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0682(200005)2000:5<901::AID-EJIC901>3.0.CO;2-A     Document Type: Article

References (44)

1. [1a] E. Negishi, Acc. Chem. Res. 1982, 75, 340-348.
2. [1b] E. Erdik, Tetrahedron 1992, 48, 9577-9648.
3. [2a] A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
4. [2b] T. N. Mitchell, Synthesis 1992, 803-815.
5. [2c] J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
6. [3a] X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
7. [3b] D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
8. [3c] A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
9. [4a] D. Villemin, E. Schigeko, J. Organomet. Chem. 1985, 293, C10-C12.
10. [4b] W. Scott, J. Chem. Soc., Chem. Commun. 1987, 1755-1756.
11. [4c] M. E. Wright, J. Organomet. Chem. 1989, 376, 353-358.
12. R. Mutin, C. Lucas, J. Thivolle-Cazat, V. Dufaud, F. Dany, J. M. Basset, J. Chem. Soc., Chem. Commun. 1988, 896-898.
13. V. Dufaud, J. Thivolle-Cazat, J. M. Basset, R. Mathieu, J. Jaud, J. Vaisserman, Organometallics 1991, 10, 4005-4015.
14. [7a] M. Uemura, H. Nishimura, T. Hayashi, Tetrahedron Lett. 1993, 34, 107-110.
15. [7b] M. Uemura, H. Nishimura, K. Kamikawa, M. Shiro, Inorganica Chimica Acta 1994, 222, 63-70.
16. [7c] M. Uemura, H. Nishimura, K. Kamikawa, K. Nakayama, Y. Hayashi, Tetrahedron Lett. 1994, 35, 1909-1912.
17. [7d] M. Uemura, K. Kamikawa, J. Chem. Soc., Chem. Commun. 1994, 2697-2698.
18. [7e] P. Caldirola, R. Chowdhury, A. M. Johansson, U. Hacksell, Organometallics 1995, 14, 3897-3900.
19. [7f] T. Watanabe, K. Kamikawa, M. Uemura, Tetrahedron Lett. 1995, 36, 6695-6698.
20. [7g] K. Kamikawa, T. Watanabe, M. Uemura, Synlett. 1995, 1040-1042.
21. [7h] M. Uemura, A. Daimon, Y. Hayashi, J. Chem. Soc., Chem. Commun. 1995, 1943-1944.
22. [7i] K. Kamikawa, T. Watanabe, M. Uemura, J. Org. Chem. 1996, 61, 1375-1384.
23. [7j] T. Watanabe, M. Uemura, Chem. Commun. 1998, 871-872.
24. F. Rose-Munch, V. Gagliardini, C. Renard, E. Rose, Coord. Chem. Rev. 1998, 178-180, 249-268.
25. F. Rose-Munch, E. Rose, Current Org. Chem. 1999, 3, 445-467.
26. D. Prim, G. Kirsch, J. Chem. Soc., Perkin Trans. 1 1994, 2603-2606.
27. Z. F. Plyta, D. Prim, J.P. Tranchier, F. Rose-Munch, E. Rose, Tetrahedron Lett. 1999, 40, 6769-6771.
28. To our knowledge, the CO inserted organometallic compound formation was reported in only one example under analogous conditions depending upon the nature of the ortho-substituent of the chromium complex (see refs. [7d], [7i]).
29. [13a] V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
30. [13b] V. Farina, B. Krishnan, D. R. Marshall, G. P. Roth, J. Org. Chem. 1993, 58, 5434-5444.
31. R. Guilard, J. Tirouflet, P. Fournari, J. Organomet. Chem. 1971, 33, 195-213.
32. [15a] J. C. Boutonnet, L. Mordenti, E. Rose, O. Le Martret, G. Precigoux, J. Organomet. Chem. 1981, 221, 147-156.
33. [15b] F. Rose-Munch, E. Rose, A. Semra, M. Philoche, J. Organomet. Chem. 1989, 363, 123-130.
34. We observed a similar effect during the study of the conformation of the tripod in solution of (2,6-dimethylchlorobenzene)-tricarbonylchromium, where no difference of shielding effect was detected for the aromatic protons (ref. [15b]).
35. 3 proton shielding are δ = 2.18 and 2.32 for complex 2 (Table 2, entry 6). These shielding effects are δ = 1.98 and 2.56 for complex 3.
36. [17b] W. R. Jackson, W. B. Jennings, S. C. Renninson, R. Spratt, J. Chem. Soc. B 1969, 1214-1221.
37. [17c] C. Segard, B. Roques, C. Pommier, G. Guiochon, Anal. Chem. 1971, 43, 1146-1151.
38. [17d] F. Van Meurs, J. M. Van der Toorn, H. Van Beckkum, J. Organomet. Chem. 1976, 113, 341-351.
39. [17e] A. Solladie-Cavallo, J. Suffert, Org. Magn. Res. 1980, 14, 426-430.
40. [17f] J. Brocard, A. Laconi, D. Couturier, Org. Magn. Res. 1984, 22, 369-371.
41. C. A. L. Mahaffy, P. L. Pauson, Inorg. Syntheses 1990, 28, 136-140.
42. G. M. Sheldrick, SHELXS-86, Program for Crystal Structure Solution, University of Göttingen, 1986.
43. D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge, Crystals, issue 10, Chemical Crystallography Laboratory, University of Oxford, U. K. 1996.
44. D. T. Cromer, International Tables for X-ray Crystallography, vol. IV, Kynoch Press, Birmingham, U. K., 1974.