New approaches in radical carbonylation chemistry: Fluorous applications and designed tandem processes by species-hybridization with anions and transition metal species

Chemical Record

Volumn 2, Issue 4, 2002, Pages 249-258

  Ryu, Ilhyong ^a  

^a Osaka City University   (Japan)

Author keywords

Carbon monoxide; Fluorous techniques; Radical carbonylation; Species hybridization; Tandem cyclization; Transition metal radical reaction

Indexed keywords

ARTICLE;

EID: 0347503391     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.10026     Document Type: Article

References (63)

1. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem Rev 1999, 99, 1991.
2. Ryu, I.; Sonoda, N. Angew Chem Int Ed Engl 1996, 35, 1050.
3. Ryu, I.; Sonoda, N.; Curran, D.P. Chem Rev 1996, 96, 177.
4. Ryu, I.; Komatsu, M. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p 93-129.
5. Ryu, I. In Radicals in Organic Syntheis, Vol. 2; Renaud, P.; Sibi, M.P, Eds.; Wiley-VCH: Weinheim, 2001; p 22-43.
6. Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J Am Chem Soc 1990, 112, 1295.
7. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
8. Curran, D.P. Synthesis, 1988, 417 (part 1);
9. Curran, D.P. Synthesis, 489 (part 2).
10. Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: London, 1992.
11. Curran, D.P.; Porter, N.A.; Giese, B. Stereochemistry of Free Radical Reactions; VCH: Weinheim, 1996.
12. Renaud, P.; Sibi, M.P., Eds. Radicals in Organic Syntheis, Vols. 1 and 2; Wiley-VCH: Weinheim, 2001.
13. Nanni, D. In Radicals in Organic Syntheis, Vol. 2; Renaud, P.; Sibi, M.P., Eds.; Wiley-VCH: Weinheim, 2001; p 44-45.
14. Yamago, S.; Miyazoe, H.; Goto, R.; Hashidume, M.; Sawazaki, T.; Yoshida, J.-I. J Am Chem Soc 2001, 123, 3697.
15. Kim, S.; Lee, I.Y.; Yoon, J.-Y.; Oh, D.H. J Am Chem Soc 1996, 118, 5138.
16. Kim, S.; Yoon, J.-Y. J Am Chem Soc 1997, 119, 5982.
17. Kim, S.; Yoon, J.-Y.; Lee, I.Y. Synlett 1997, 475.
18. Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J Am Chem Soc 1993, 115, 1187.
19. Ryu, I.; Kuriyama, H.; Minakata, S.; Komatsu, M.; Yoon, J.-Y.; Kim, S. J Am Chem Soc 1999, 121, 12190.
20. Ryu, I. Chem Soc Rev 2001, 30, 16.
21. Horváth, I.T. Acc Chem Res 1998, 31, 641.
22. Curran, D.P. Angew Chem Int Ed Engl 1998, 37, 1174.
23. Barthel-Rosa, L.P.; Gladysz, J.A. Coord Chem Rev 1999, 192, 587.
24. Curran, D.P.; Hadida, S. J Am Chem Soc 1996, 118, 2531.
25. Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D.P. Tetrahedron Lett 1997, 38, 7883.
26. Horner, J.H.; Martinez, F.N.; Newcomb, M.; Hadida, S.; Curran, D.P. Tetrahedron Lett 1997, 38, 2783.
27. Curran, D.P.; Luo, Z.; Degenkolb, P. Bioorganic Med Chem Lett 1998, 8, 2403.
28. Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D.P. Tetrahedron Lett 1999, 40, 2367.
29. Gupta, V.; Kahne, D. Tetrahedron Lett 1993, 34, 591.
30. Matsubara, H.; Yasuda, S.; Sugiyama, H.; Ryu, I.; Fujii, Y.; Kita, K. Tetrahedron, 2002, 58, 4071.
31. Curran, D.P. Synlett 2001, 1488.
32. Ryu, I.; Kreimerman, S.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D.P. Tetrahedron Lett 2001, 42, 947.
33. Alvey, L.J.; Rutherford, D.; Juliette, J.J.J.; Gladysz, J.A. J Org Chem 1998, 63, 6302.
34. Molander, G.A. Chem Rev 1992, 92, 29.
35. Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M. J. Synlett 1992, 943.
36. Iqbal, J.; Bhatia, B.; Nayyar, N.K. Chem Rev 1994, 94, 519.
37. Dalko, P.I. Tetrahedron 1995, 51, 7579.
38. Molander, G.A.; Harris, C.R. Chem Rev 1996, 96, 307.
39. Shono, T.; Nishiguchi, I.; Sasaki, M. J Am Chem Soc 1978, 100, 4314.
40. Takai, K.; Ueda, T.; Ikeda, N.; Moriwake, T. J Org Chem 1996, 61, 7990.
41. Takai, K. J Org Chem 1996, 61, 8728.
42. Molander, G.A.; Harris, C.R. J Am Chem Soc 1996, 118, 4059.
43. Tsunoi, S.; Ryu, I.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Synlett 1995, 1249.
44. Rathke, M.W.; Yu, H. J Org Chem 1972, 37, 1732.
45. Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N. Komatsu, M. Chem Commun 1997, 1889.
46. Ogawa, A.; Sumino, Y.; Nanke, T.; Ohya, S.; Sonoda, N.; Hirao, T. J Am Chem Soc 1997, 119, 2745.
47. Negishi, E.; Copérer, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J.M. J Am Chem Soc 1996, 118, 5904.
48. Grigg, R.; Sridharan, V. J. Organomet Chem 1999, 576, 65.
49. Luh, T.-Y.; Leung, M.; Wong, K.T. Chem Rev 2000, 100, 3187.
50. Cárdenas, D.J. Angew Chem Int Ed Engl 1999, 38, 3018.
51. Netherton, M.R.; Dai, C.; Neuschürz; Fu, G.C. J Am Chem Soc 2001, 123, 10099.
52. Giovannini, R.; Stüdemann, T.; Dussin, G.; Knochel, P. J Org Chem 1999, 64, 3544.
53. Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J Am Chem Soc 1997, 119, 5465.
54. Ryu, I.; Nagahara, K.; Kambe, N.; Sonoda, N.; Kreimerman, S.; Komatsu, M. Chem Commun 1998, 1953.
55. Kreimerman, S.; Ryu, I.; Minakata, S.; Komatsu, M. Org Lett 2000, 2, 389.
56. Ryu, I.; Kreimerman, S.; Araki, F.; Nishitani, S.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. J Am Chem Soc, 2002, 124, 3812.
57. Beckwith, A.L.J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
58. Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J Am Chem Soc 1996, 118, 10670.
59. Yamamoto, A. Bull Chem Soc Jpn 1995, 68, 433.
60. Yamamoto, A. J Chem Soc Dalton Trans 1999, 1027.
61. Lin, Y.-S.; Yamamoto, A. Organometallics 1998, 17, 3466.
62. T. Kondo, T.; Sone, Y.; Tsuji, Y.; Watanabe, Y.J. Organomet Chem 1994, 473, 163.
63. Ishiyama, T.; Murata, M.; Suzuki, A.; Miyaura, N. J Chem Soc Chem Commun 1995, 295.