New examples of 1,6- and 1,7-hydrogen transfer promoted by an α-silyl group in rhodium(I)-catalyzed radical reactions of acyclic enediynes

Organometallics

Volumn 17, Issue 14, 1998, Pages 2942-2944

  Manabe, Takao ^a   Yanagi, Shin Ichi ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000782213     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980143i     Document Type: Article

References (50)

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2. Lambert, J. B. Tetrahedron 1990, 46, 2677 and references therein.
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4. For reviews, see: (a) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 563-593. (b) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Sarkar, T. K. Synthesis 1990, 969.
5. For reviews, see: (a) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 563-593. (b) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Sarkar, T. K. Synthesis 1990, 969.
6. For reviews, see: (a) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 563-593. (b) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Sarkar, T. K. Synthesis 1990, 969.
7. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
8. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
9. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
10. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
11. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
12. For β-silicon stabilization, see: (a) Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208. (b) Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207. (c) Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644. (d) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281. (e) Hwu, J. R.; Chen, B.-L.; Shiao, S.-S. J. Org. Chem. 1995, 60, 2448. (f) Zhang, S.; Bordwell, F. G. J. Org. Chem. 1996, 61, 51.
13. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
14. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
15. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
16. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
17. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
18. For α-silicon stabilization, see refs 4c,d and: (a) Wilt, J. W.; Kolewe, O. J. Am. Chem. Soc. 1965, 87, 2071. (b) Krusic, P. J.; Kochi, J. K. J. Am. Chem. Soc. 1969, 91, 6161. (c) Sakurai, H.; Hosomi, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1971, 44, 568. (d) Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285. (e) Wetzel, D. M.; Brauman, J. I. J. Am. Chem. Soc. 1988, 110, 8333. (f) Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4413.
19. For examples suggesting that silyl groups scarcely stabilize α-carbon-centered radicals, see: (a) Doncaster, A. M.; Walsh, R. J. Chem. Soc., Faraday Trans. 1 1976, 72, 2908. (b) Zhang, S.; Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1995, 117, 602.
20. For examples suggesting that silyl groups scarcely stabilize α-carbon-centered radicals, see: (a) Doncaster, A. M.; Walsh, R. J. Chem. Soc., Faraday Trans. 1 1976, 72, 2908. (b) Zhang, S.; Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1995, 117, 602.
21. For reviews, see: (a) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (b) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (c) Smadja, W. Synlett 1994, 1. (d) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143. (e) Bachi, M. D.; Balanov, A.; Ber-Ner, N.; Bosch, E.; Denenmark, D.; Mizhiritskii, M. Pure Appl. Chem. 1993, 65, 595. (f) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (g) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 745-832.
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30. (a) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995. (b) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057. (c) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907.
31. (a) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995. (b) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057. (c) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907.
32. (a) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995. (b) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057. (c) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907.
33. Ohe, K.; Kojima, M.; Yonehara, K.; Uemura, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1823.
34. For cascade radical reactions via α,3-didehydrotoluene diradicals, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453 and references therein. (b) Wang, K. K. Chem. Rev. 1996, 96, 207. (c) Wang, K. K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783.
35. For cascade radical reactions via α,3-didehydrotoluene diradicals, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453 and references therein. (b) Wang, K. K. Chem. Rev. 1996, 96, 207. (c) Wang, K. K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783.
36. For cascade radical reactions via α,3-didehydrotoluene diradicals, see: (a) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453 and references therein. (b) Wang, K. K. Chem. Rev. 1996, 96, 207. (c) Wang, K. K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783.
37. 1,6-Transfer: (a) Wagner, P. J.; Chiu, C. J. Am. Chem. Soc. 1979, 101, 7134. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1986, 1165. (c) Yamazaki, N.; Eichenberger E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (d) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142. (e) Bogen, S.; Fensterbank L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
38. 1,6-Transfer: (a) Wagner, P. J.; Chiu, C. J. Am. Chem. Soc. 1979, 101, 7134. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1986, 1165. (c) Yamazaki, N.; Eichenberger E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (d) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142. (e) Bogen, S.; Fensterbank L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
39. 1,6-Transfer: (a) Wagner, P. J.; Chiu, C. J. Am. Chem. Soc. 1979, 101, 7134. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1986, 1165. (c) Yamazaki, N.; Eichenberger E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (d) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142. (e) Bogen, S.; Fensterbank L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
40. 1,6-Transfer: (a) Wagner, P. J.; Chiu, C. J. Am. Chem. Soc. 1979, 101, 7134. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1986, 1165. (c) Yamazaki, N.; Eichenberger E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (d) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142. (e) Bogen, S.; Fensterbank L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
41. 1,6-Transfer: (a) Wagner, P. J.; Chiu, C. J. Am. Chem. Soc. 1979, 101, 7134. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1986, 1165. (c) Yamazaki, N.; Eichenberger E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (d) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142. (e) Bogen, S.; Fensterbank L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
42. 1,7-Transfer: Fensterbank, L.; Dhimane, A.-L.; Wu, S.; Lacôte, E.; Bogen, S.; Malacria, M. Tetrahedron 1996, 52, 11405.
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46. 10
47. +) calcd 176.1021, found 176.1018.
48. -1, respectively; see: Dorigo, A. E.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 2195.
49. Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421.
50. Some π-acids accelerate the reductive elimination of some 16-electron organopalladium species, providing C-C bonds: Kurosawa, H.; Emoto, M.; Ohnishi, H.; Miki, K.; Kasai, N.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1987, 109, 6333.