Nickel catalyzed tellurium-zinc exchange reactions. A new preparation of arylzinc reagents

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1005-1008

  Stüdemann, Thomas ^a   Gupta, Vijay ^b   Engman, Lars ^b   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02482-3     Document Type: Article

References (61)

1. 1. (a) Knochel, P.; Singer, R. Chem. Rev. 1993, 93, 2117.
2. (b) Knochel, P. Synlett 1995, 393.
3. 2. (a) Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143.
4. (b) Eisenberg, C.; Knochel, P. J. Org. Chem. 1994, 59, 3760.
5. (c) Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849.
6. (d) Knochel, P.; Vettel, S.; Eisenberg, C. Applied. Organomet. Chem. 1995, 9, 175.
7. 3. (a) Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
8. (b) Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Synlett 1994, 410.
9. 4. (a) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777.
10. (b) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
11. (c) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593.
12. 5. (a) Stadtmüller, H.; Lentz, R.; Dörner, W.; Stüdemann, T.; Tucker, C. E.; Knochel, P. J. Am. Chem Soc. 1993, 115, 7027.
13. (b) Stadtmüller, H.; Tucker, C. E.; Vaupel, A.; Knochel, P. Tetrahedron Lett. 1993, 34, 7911.
14. (c) Klement, I.; Chau, K.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1994, 55, 1177.
15. (d) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
16. (e) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231.
17. (f) Stadtmüller, H.; Knochel, P. Synlett 1995, 463.
18. (g) Stadtmüller, H.; Vaupel, A.; Tucker, C. E.; Stüdemann, T.; Knochel, P. Chem. Eur. J. 1996, 2, 108.
19. (h) Riguet, E.; Klement, I.; Reddy, K. C.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1996, 37, 5865.
20. 6. For transition metal promoted carbodetelluration reactions of organotellurium compounds see: (a) Bergman, J. Tetrahedron 1972, 28, 3323.
21. (b) Bergman, J.; Engman, L. J. Organomet. Chem. 1979, 175, 233.
22. (c) Bergman, J.; Engman, L. Tetrahedron 1980, 36, 1275.
23. (d) Uemura, S.; Fukuzawa, S.-I.; Patil, S. R. J. Organomet. Chem. 1983, 243, 9.
24. (e) Wenkert, E.; Leftin, M. H.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1984, 617.
25. (f) Ohe, K.; Takahashi, H.; Uemura, S.; Sugita, N. J. Org. Chem. 1987, 52, 4859.
26. (g) Barton, D. H. R.; Ozbalik, N.; Ramesh, M. Tetrahedron Lett. 1988, 29, 3533.
27. (h) Nishibayashi, Y.; Cho, C. S.; Uemura, S. J. Organomet. Chem. 1996, 507, 197.
28. 7. For a tellurium-zinc exchange reaction allowing the preparation of alkenylzinc derivatives, see: Terao, J.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1996, 37, 4741.
29. 8. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
30. 9. (a) Engman, L. Acc. Chem. Res. 1985, 18, 274.
31. (b) Engman, L. Organometallics 1986, 5, 427.
32. (c) Petragnani, N. in Comprehensive Organometallic Chemistry II, Eds. A. McKillop, Pergamon, 1995, Volume 11, p. 571-602.
33. (d) Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1. 10.
34. (a) Barros, S. M.; Comasseto, J. V.; Berriel, J. Tetrahedron Lett. 1989, 30, 7353.
35. (b) Hiiro, T.; Atarashi, Y.; Kambe, N.; Fujiwara, S.; Ogawa, A.; Ryn, I.; Sonoda, N. Organometallics 1990, 9, 1355.
36. (b) Comasseto, J. V.; Berriel, J. N. Synth. Commun. 1990, 20, 1681.
37. (c) Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1991, 113, 1414.
38. (d) Nakahira, H.; Ryu, I. Han, L. Kambe, N.; Sonoda, N. Tetrahedron Lett. 1991, 32, 229.
39. (e) Kanda, T.; Kato, S.; Sugino, T.; Kambe, N.; Sonoda, N. J. Organomet. Chem. 1994, 473, 71.
40. (f) Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1994, 35, 4063.
41. (g) Strohmann, C. Angew. Chem. 1996, 108, 600.
42. (h) Terao, J.; Kambe, N.; Sonoda, N, Synlett 1996, 779.
43. (i) Tucci, F. C; Chieffi, A.; Comasseto, J. V.; Marino, J. P. J. Org. Chem. 1996, 61, 4975.
44. 11. Te-Li exchange: (a) Hiro, T.; Kambe, N.; Ogawa, A.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem. 1987, 99, 1221.
45. (b) Engman, L.; Stern, D. Organometallics 1993, 12, 1445.
46. (c) Kanda, T.; Kato, S.; Sugino, T.; Kambe, N.; Sonoda, N. J. Organomet. Chem. 1994, 473, 71.
47. (d) Strohmann, C. Angew. Chem. 1996, 108, 600. Te-Cu exchange:
48. (e) Tucci, F. C.; Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 5721.
49. (f) Ogawa, A.; Tsuboi, Y.; Obayashi, R.; Yokoyama, K.; Ryu, I.; Sonoda, N. J. Org.Chem. 1994, 59, 1600.
50. (g) Chieffi, A.; Comasseto, J. V. Tetrahedron Lett. 1994, 35, 4063.
51. (h) Chieffi, A.; Comasseto, J. V. Synlett 1995, 671.
52. (i) Tucci, F. C.; Chieffi, A.; Comasseto, Y. V.; Marino, J. P. J. Org. Chem. 1996, 61, 4975. Te-Al exchange:
53. (j) Terao, J.; Kambe, N.; Sonoda, N. Synlett 1996, 779.
54. 12. (a) Negishi, E. Ace. Chem. Res. 1982, 15, 340.
55. (b) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc.; Chem. Commun. 1972, 144.
56. (c) Tamo, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
57. 13. Devasagayaraj, A.; Stüdemann, T.; Knochel, P. Angew. Chem. 1995, 107. 2952.
58. 14. Engman, L.; Gupta, V. J. Chem. Soc. Chem. Commun. 1995, 2515.
59. 2Zn (1.5 mL, 15 mmol, 5 equiv) was slowly added via syringe. The reaction was allowed to warm to rt and was stirred for 6 h. Meanwhile a mixture of copper cyanide (2.68 g, 23 mmol) and lithium chloride (2.54 g, 60 mmol) was dried under vacuum (130 °C, 2 h) and dissolved in THF (10 mL). This solution was added to this reaction mixture at -60 °C, followed by 2,3-dibromopropene (6.0 g, 30 mmol, 10 equiv). The reaction mixture was warmed up to rt and worked up as usual. The crude oil obtained after evaporation of the solvents was purified by flash chromatography (hexanes) affording 5g (1.45 g, 5.2 mmol, 88 % yield) as a colorless oil.
60. 16. Engman, L.; Persson, J. J. Organomet. Chem. 1990, 388, 71.
61. 17. Tentative reaction mechanism. (equaton presented)