Sequential generation and utilization of radical and anionic species with a novel manganese-lead reducing agent. Three-component coupling reactions of alkyl iodides, electron-deficient olefins, and carbonyl compounds

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7990-7991

  Takai, Kazuhiko ^a   Ueda, Takashi ^a   Ikeda, Norihiko ^a   Moriwake, Toshio ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344148437     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9617530     Document Type: Article

References (29)

1. For some reviews of representative examples of serial processes with different intermediates, see: Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Malacria, M. Chem. Rev, 1996, 96, 289; Snider, B. B. Chem. Rev. 1996, 96, 339.
2. For some reviews of representative examples of serial processes with different intermediates, see: Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Malacria, M. Chem. Rev, 1996, 96, 289; Snider, B. B. Chem. Rev. 1996, 96, 339.
3. For some reviews of representative examples of serial processes with different intermediates, see: Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. Malacria, M. Chem. Rev, 1996, 96, 289; Snider, B. B. Chem. Rev. 1996, 96, 339.
4. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
5. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
6. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
7. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
8. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
9. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
10. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872; Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
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27. 3SiCl was also effective in promoting the reaction.
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