Diethylzinc: A chain-transfer agent in intermolecular radical additions. A parallel with triethylborane

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9189-9193

  Bertrand, Michèle P ^a   Feray, Laurence ^a   Nouguier, Robert ^a   Perfetti, P ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; METHACRYLIC ACID METHYL ESTER; ZINC DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0032784299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912404     Document Type: Article

References (52)

1. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. Synlett 1999, 1148-1150.
2. 2Zn, see: Ryu, I.; Araki, F.; Minakata, S.; Komatau, M. Tetrahedron Lett. 1998, 39, 6335-6336.
3. 2, see: Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422.
4. Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780-782.
5. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
6. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
7. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431-11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
8. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
9. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
10. 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
11. (a) Van Vliet, M. R. P.; Van Koten, G.; Buysingh, P.; Jastrzebski, J. T. B. H.; Spek, A. L. Organometallics 1987, 6, 537-546.
12. (b) Van Vliet, M. R. P.; Jastrzebski, J. T. B. H.; Klaver, W. J.; Goubitz, K.; Van Koten, G. Recl. Trav. Chim. Pays-Bas 1987, 106, 132-134.
13. (c) Wissing, E.; Havenith, R. W. A.; Boersma, J.; Van Koten, G. Tetrahedron Lett. 1992, 33, 7933-7936.
14. 4c have reported the incorporation of two ethyl groups via, respectively, C-C and C-N bond formation, in the triethylborane-promoted addition of ethyl radical to 3. However, in this case the N-alkylated product resulted from nucleophilic substitution of ethyl iodide (used as coreagent) by 8a.
15. Kim, S. Tetrahedron 1997, 53, 73-80.
16. Nagashima, T.; Curran, D. P. Synlett 1996, 330-332.
17. (a) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633.
18. (b) Hart, D. J.; Krishnamurthy, R.; Pook, L. M.; Seely, F. L. Tetrahedron Lett. 1993, 34, 7819-7822.
19. (c) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199.
20. (a) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139.
21. (b) Kim, S.; Yoon, J.-Y.; Lee, I. Y. Synlett 1997, 475-476.
22. Russell, G. A.; Wang, L.; Rajaratnam, R. J. Org. Chem. 1996, 61, 8988-8991.
23. (a) Hanessian, S.; Yang, R.-H. Tetrahedron Lett. 1996, 37, 8997-9000.
24. (b) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489-8490.
25. (c) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186-195 and refs cited therein.
26. Hou, X. L.; Zhen, X. L.; Dai, L. X. Tetrahedron Lett. 1998, 38, 6949-6952.
27. (a) Katritzky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437-442.
28. (b) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097-1098.
29. (c) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519-2522.
30. (d) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364-7375.
31. (e) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530-2535.
32. (f) Jimeno, C.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 777-780.
33. (a) Brown, H. C.; Kabalka, G. W. J. Am. Chem. Soc. 1970, 92, 714-716.
34. (b) Brown, H. C.; Negishi, E. J. Am. Chem. Soc. 1971, 93, 3777-3779.
35. B-Alkylcatecholboranes, readily available from the reaction of various olefins and catecholborane, have been used to perform radical additions to α,β-unsaturated ketones and aldehydes. See: Ollivier, C.; Renaud, P. Chem. Eur. J. 1999, 5, 1468-1473.
36. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
37. For general reviews on organozinc mediated reactions see: (a) Knochel, P.; Almene Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275-8319. (b) Knochel, P. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds; Wiley- VCH: Weinheim, 1998; Vol. 1, pp 467-503.
38. For general reviews on organozinc mediated reactions see: (a) Knochel, P.; Almene Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275- 8319. (b) Knochel, P. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 467-503.
39. For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
40. For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
41. For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
42. For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
43. 2Zn could promote asymmetric epoxidation of enones and nitro alkenes; see: (a) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann. 1997, 1101-1113. (b) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959-3962.
44. 2Zn could promote asymmetric epoxidation of enones and nitro alkenes; see: (a) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann. 1997, 1101-1113. (b) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959-3962.
45. (a) Velarde-Ortiz, R.; Guijarro, A.; Rieke, R. D. Tetrahedron Lett. 1998, 39, 9157-9160.
46. (b) Guijarro, A.; Rieke, R. D. Angew. Chem., Int. Ed. Engl. 1998, 37, 1679-1681.
47. 3B behaves as a reducing reagent.
48. Barreau, M.; Commerçon, A.; Mignani, S.; Mouysset, D.; Perfetti, P.; Stella, L. Tetrahedron 1998, 54, 11501-11516.
49. Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5431-5440.
50. Nonkunsarn, P.; Ramsden, C. A. Tetrahedron 1997, 53, 3805-3830.
51. Shimizu, K.; Nakayama, K.; Akiyama, M. Bull. Chem. Soc. Jpn. 1984, 57, 2456-2462.
52. Wheeler, O. H. J. Org. Chem. 1964, 29, 3634-3636.