Radical-polar crossover domino reactions involving organozinc and mixed organocopper/organozinc reagents

Chemistry - A European Journal

Volumn 12, Issue 25, 2006, Pages 6506-6513

  Denes, Fabrice ^a   Cutri, Sabrina ^a   Perez Luna, Alejandro ^a   Chemla, Fabrice ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Copper; Domino reactions; Michael addition; Radical reactions; Zinc

Indexed keywords

ADDITION REACTIONS; COPPER COMPOUNDS; HALOGEN COMPOUNDS; NITROGEN COMPOUNDS; ORGANOMETALLICS; ZINC COMPOUNDS;

CROSSOVER MECHANISM; DIORGANOZINC REAGENTS; DOMINO REACTIONS; MICHAEL ADDITION; ORGANOCOPPER; RADICAL REACTIONS;

REACTION KINETICS;

EID: 33748542017     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600334     Document Type: Article

References (50)

1. F. Denes, F. Chemla, J. F. Normant, Synlett 2002, 919-922.
2. E. Sliwinski, F. Denes, F. Chemla, J. F. Normant, C. R. Chim. 2003, 67-78.
3. a) F. Orsini, F. Pelizzoni, G. Ricca, Tetrahedron Lett. 1982, 23, 3945-3948;
4. b) J. Boersma, J. Dekker, G. J. M. van der Kerk, J. Chem. Soc. Chem, Commun. 1983, 553-555;
5. c) J. Boersma, P. H. M. Budzelaar, J. Dekker, G. J. M. van der Kerk, Organometallics 1984, 3, 1403-1407;
6. d) F. Orsini, F. Pelizzoni, G. Ricca, Tetrahedron 1984, 40 2781-2787.
7. F. Denes, F. Chemla, J. F. Normant, Eur. J. Org. Chem. 2002, 3536-3542.
8. F. Denes, F. Chemla, J. F. Normant, Angew. Chem. 2003, 115, 4177-4180;
9. Angew. Chem. Int. Ed. 2003, 42, 4043-4046.
10. For other examples of oxygen-induced 1,4-addition of dialkylzinc reagents, see: a) M. P. Bertrand, R. Feray, R. Nouguier, P. Perfetti, J. Org. Chem. 1999, 64, 9189-9193;
11. b) B. L. Feringa, R. M. Kellog, H. van der Deen, Org. Lett. 2000, 2, 1593-1595;
12. c) S. Bazin, L. Feray, D. Siri, J.-V. Naubron, M. P. Bertrand, Chem. Commun. 2002, 2506-2507;
13. d) H. Miyabe, R. Asada, K. Yoshida, Y. Takemoto, Synlett 2004, 540-542;
14. e) H. Miyabe, R. Asada, Y. Takemoto, Tetrahedron 2005, 61, 385-393;
15. f) S. Bazin, L. Feray, N. Vanthuyne, M. P. Bertrand, Tetrahedron 2005, 61, 4261-4274.
16. For related examples involving oxygen-induced radical reactions of dialkylzinc compounds, see: a) I. Ryu, F. Araki, S. Minakata, M. Komatsu, Tetrahedron Lett. 1998, 39, 6335-6336;
17. b) M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, Synlett 1999, 1148-1150;
18. c) M. P. Bertrand, S. Coantic, L. Feray, R. Nouguier, P. Perfetti, Tetrahedron 2000, 56, 3951-3961;
19. d) H. Miyabe, C. Ushiro, M. Ueda, K. Yamakawa, T. Naito, J. Org. Chem. 2000, 65, 176-185;
20. e) H. Miyabe, C. Konishi, T. Naito, Org. Lett. 2000, 2, 1443-1445;
21. f) K. Yamada, H. Fujihara, Y. Yamamoto, Y. Miwa, T. Taga, K. Tomioka, Org. Lett. 2002, 4, 3509-3511;
22. g) K. Yamada, Y. Yamamoto, K. Tomioka, Org. Lett. 2003, 5, 1797-1799;
23. h) H. Miyabe, A. Nishimura, Y. Fujishima, T. Naito, Tetrahedron 2003, 59, 1901-1907
24. i) K. Yamada, Y. Yamamoto, Y. Miwa, M. Maekawa, K. Tomioka, J. Org. Chem. 2004, 69, 1531-1534;
25. j) K. Yamada, Y. Yamamoto, M. Maekawa, T. Akindele, H. Umeki, K. Tomioka, Org. Lett. 2006, 8, 87-89.
26. a) S. Kim, J. M. Lee, Tetrahedron Lett. 1990, 37, 7627-7630;
27. b) M. V. Hanson, R.D. Rieke, J. Am. Chem. Soc. 1995, 117, 10775-10776;
28. c) A. Devasagayaraj, P. Knochel, K. Reddy, Tetrahedron Lett. 1996, 37, 4495-4498.
29. It is conceivable that if a fast equilibrium exists, iPrM, although less stable than nBuM, could react much faster than nBuM and thus distort our scrambling experiments.
30. a) A. B. Charette, A. Beauchemin, J.-F. Marcoux, J. Am. Chem. Soc. 1998, 120, 5114-5115;
31. b) A. B. Charette, A. Beauchemin, J.-F. Marcoux, Tetrahedron Lett. 1999, 40, 33-36.
32. M.J. Rozema, C. Eisenberg, H. Lütjens, R. Ostwald, K. Belyk, P. Knochel, Tetrahedron Lett. 1993, 34, 3115-3118.
33. a) D. P. Curran in Comprehensive Organic Chemistry, Vol. 4 (Eds.: B. M. Trost, I. Fleming,) Pergamon Press, 1991, pp. 779-831;
34. b) T. V. Rajanbabu, Acc. Chem. Res. 1991, 24, 139-145.
35. a) R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860;
36. b) D. J. Hart, R. Krishnamurthy, Synlett 1991, 412-414;
37. c) M. Bulliard, B. Giese, H. G. Zeitz, Synlett 1991, 425-427;
38. d) W. Smadja, Acc. Chem. Res. 1994, 27, 1-26;
39. e) R. Batra, W. Damm, B. Giese, ChemTracts 1994, 7, 355-370.
40. For related recent selected examples of domino radical-polar crossover reactions, see; a) D. C. Harowwen, M. C. Lucas, P.D. Howes, Tetrahedron 2001, 57, 791-804;
41. b) A. Rivkin, F. Gonzalez-Lopez de Turiso, T. Nagashima, D. P. Curran, J. Org. Chem. 2004, 69, 3719-3725;
42. c) U. Jahn, D. Rudakov, Synlett 2004, 1207-1210;
43. d) M. Ueda, H. Miyabe, H. Sugino, O. Miyata, T. Naito, Angew. Chem. 2005, 117, 6346-6349;
44. Angew. Chem. Int. Ed. 2005, 44, 6190-6193.
45. For a review, see: G. S. C. Srikanth, S. L. Castle, Tetrahedron 2005, 61, 10377-10441.
46. For a recent report concerning radical reactions in organocopper 1,4-additions, see: J. Yang, D.F. Cauble, A. J. Berro, N.L. Bauld, M. J. Krische, J. Org. Chem. 2004, 69, 7979-7984.
47. I salts, see: a) K. Agapiou, D. F. Cauble, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 4528-4529;
48. b) K. Li, A. Alexakis, Tetrahedron Lett. 2005, 46, 5823-5826;
49. c) K. Li, A. Alexakis, Tetrahedron Lett. 2005, 46, 8019-8022.
50. A. Dondoni, F. L. Merchan, P. Merino, T. Tejero, Synth. Commun. 1994, 24, 2551-2555.