Highly selective radical reactions of sulfonyl chlorides catalyzed by a ruthenium(II) complex

Reviews on Heteroatom Chemistry

Volumn 17, Issue , 1997, Pages 1-50

  Kamigata, Nobumasa ^a   Shimizu, Toshio ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

Addition; Asymmetric addition; Desulfonylation; Perfluoroalkylation; Radical reaction; Ruthenium(II) catalyzed reaction; Sulfonyl chloride

Indexed keywords

EID: 0011554926     PISSN: 09156151     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (77)

1. M. S. Kharasch, H. Engelmann and F. R. Mayo: J. Org. Chem. 2 288 (1937).
2. a) C. Walling: Free Radicals in Solution (Wiley, New York, 1957);
3. b) C. Walling and E. S. Huyser: Org. Reac. 13 91 (1963);
4. c) G. Sosnovsky: Free Radical Reactions in Preparative Organic Chemistry (Macmillan, New York, 1964);
5. d) W. A. Pryor: Introduction to Free Radical Reactions (Wiley Interscience, New York, 1970);
6. f) J. M. Hay: Reactive Free Radical (Academic Press, New York, 1974);
7. g) D. I. Davis and M. J. Parrott: Free Radicals in Organic Synthesis (Springer-Verlag, New York, 1978).
8. a) J. K. Kochi: Organometallic Mechanisms and Catalysis (Academic Press, New York, 1978);
9. b) Y. Mori and J. Tsuji: Kagaku no Ryoiki 27 197 (1973);
10. c) H. Matsumoto and Y. Nagai: Kagaku no Ryoiki 30 50 (1976);
11. d) Y. Nagai and H. Matsumoto: "How to Control the Organic Synthetic Reactions" in Kagaku Sosetu (Chem. Soc. Jpn.) 47 100 (1985).
12. a) M. Asscher and D. Vofsi: J. Chem. Soc. 1887 (1963);
13. b) M. Asscher and D. Vofsi: J. Chem. Soc. 3921 (1963).
14. a) H. Matsumoto, T. Nakano and Y. Nagai: Tetrahedron Lett. 5147 (1973);
15. b) H. Matsumoto, T. Nikaido and Y. Nagai: Tetrahedron Lett. 899 (1975);
16. c) H. Matsumoto, T. Nikaido and Y. Nagai: J. Org. Chem. 41 396 (1976);
17. d) T. Nakano, H. Arai, H. Matsumoto and Y. Nagai: Org. Prep. Proc. 10 55 (1978);
18. e) H. Matsumoto, T. Nakano, Y. Nagai and H. Kono: Bull. Chem. Soc. Jpn. 51 2445 (1978);
19. f) H. Matsumoto, T. Nakano, T. Nikaido and Y. Nagai: Chem. Lett. 115 (1978);
20. g) H. Matsumoto, T. Nakano, K. Takasu and Y. Nagai: J. Org. Chem. 43 1734 (1978);
21. h) H. Matsumoto, T. Nakano, K. Ohkawa and Y. Nagai: Chem. Lett. 363 (1978);
22. i) H. Matsumoto, T. Motegi, T. Nakano and Y. Nagai: J. Organomet. Chem. 174 157 (1979);
23. j) H. Matsumoto, K. Ohkawa, S. Ikemori, T. Nakano and Y. Nagai: Chem. Lett. 1011 (1979);
24. k) T. Nakano, Y. Shimada, R. Sako, M. Kayama, H. Matsumoto and Y. Nagai: Chem. Lett. 1255 (1982).
25. S. J. Cristol and J. A. Reeder; J. Org. Chem. 26 2182 (1961).
26. M. Asscher and D. Vofsi; J. Chem. Soc. 4962 (1964).
27. Y. Amiel: J. Org. Chem. 39 3867 (1974) and references cited therein.
28. N. Kamigata, H. Sawada, N. Suzuki and M. Kobayashi: Phosphorus and Sulfur 19 199 (1984).
29. a) N. Kamigata, H. Sawada and M. Kobayashi: Chem. Lett. 131 (1979);
30. b) N. Kamigata, H. Sawada and M. Kobayashi: J. Org. Chem. 48 3793 (1983);
31. c) N. Kamigata, T. Narushima, H. Sawada and M. Kobayashi: Bull. Chem. Soc. Jpn. 57 1421 (1984).
32. M. Kosugi, K. Kurino, K. Takayama and T. Migita: J. Organomet. Chem. 56 C11 (1973); T. Migita, M. Kosugi, K. Takayama and Y. Nakagawa: Tetrahedron 29 51 (1973); M. Kosugi, Y. Shimizu and T. Migita: J. Organomet. Chem. 129 C36 (1977).
33. M. Kosugi, K. Kurino, K. Takayama and T. Migita: J. Organomet. Chem. 56 C11 (1973); T. Migita, M. Kosugi, K. Takayama and Y. Nakagawa: Tetrahedron 29 51 (1973); M. Kosugi, Y. Shimizu and T. Migita: J. Organomet. Chem. 129 C36 (1977).
34. M. Kosugi, K. Kurino, K. Takayama and T. Migita: J. Organomet. Chem. 56 C11 (1973); T. Migita, M. Kosugi, K. Takayama and Y. Nakagawa: Tetrahedron 29 51 (1973); M. Kosugi, Y. Shimizu and T. Migita: J. Organomet. Chem. 129 C36 (1977).
35. N. Kamigata, K. Ishii, T. Ohtsuka and H. Matsuyama: Bull. Chem. Soc. Jpn. 64 3479 (1991).
36. N. Kamigata, N. Suzuki and M. Kobayashi: Phosphorus, Sulfur and Silicon 20 139 (1984).
37. a) J. Blum: Tetrahedron Lett. 3041 (1966);
38. b) J. Blum and G. Schart: J. Org. Chem. 35 1895 (1970).
39. M. L. Poutuma and P. A. Ibarbia: J. Org. Chem. 34 2848 (1969).
40. N. Kamigata, H. Sawada, J. Ozaki and M. Kobayashi: Sulfur Lett. 1 131 (1983).
41. a) R. Filler and Y. Kobayashi: Biomedicinal Aspects of Fluorine Chemistry (Elsevier Biomedical Press and Kodansha Ltd. 1982);
42. b) J. T. Welch: Tetrahedron 43 3123 (1987);
43. M. Hudlicky: Chemistry of Organic Fluorine Compounds (Ellis Horwood, New York, 1976);
44. R. E. Banks: Organofluorine Chemicals and Their Industrial Applications (Ellis Horwood, London, 1979).
45. a) N. Kamigata, T. Fukushima and M. Yoshida: J. Chem. Soc., Chem. Commun. 1559 (1989);
46. b) N. Kamigata, T. Fukushima, Y. Terakawa, M. Yoshida and H. Sawada: J. Chem. Soc., Perkin Trans. 1 627 (1991).
47. a) K. Uneyama and K. Ueda: Chem. Lett. 853 (1988);
48. b) N. Muller: J. Org. Chem. 48 1370 (1983), 49 2826 (1984), 49 4559 (1984), 51 263 (1986);
49. b) N. Muller: J. Org. Chem. 48 1370 (1983), 49 2826 (1984), 49 4559 (1984), 51 263 (1986);
50. b) N. Muller: J. Org. Chem. 48 1370 (1983), 49 2826 (1984), 49 4559 (1984), 51 263 (1986);
51. b) N. Muller: J. Org. Chem. 48 1370 (1983), 49 2826 (1984), 49 4559 (1984), 51 263 (1986);
52. c) M. Yoshida, N. Kamigata, H. Sawada and M. Nakayama: J. Fluorine Chem. 49 1-20 (1990) and references cited therein.
53. M. Yoshida, K. Moriya, H. Sawada and M. Kobayashi: Chem. Lett. 755 (1985).
54. N. Kamigata, T. Fukushima and M. Yoshida: Chem. Lett. 649 (1990).
55. a) N. Kamigata, T. Ohtsuka and T. Shimizu: Sulfur Lett. 17 69 (1994);
56. b) N. Kamigata, T. Ohtsuka, M. Yoshida and T. Shimizu: Synthetic Commun. 24 2049 (1994);
57. c) N. Kamigata, T. Ohtsuka, T. Fukushima, M. Yoshida and T. Shimizu: J. Chem. Soc., Perkin Trans. 1 1339 (1994);
58. d) N. Kamigata, T. Ohtsuka and T. Shimizu: Phosphorus, Sulfur and Silicon 95 491 (1994).
59. N. Kamigata, M. Yoshikawa and T. Shimizu: Phosphorus, Sulfur and Silicon in press.
60. N. Kamigata, M. Yoshikawa and T. Shimizu: J. Fluorine Chem. in press.
61. a) N. Kamigata, J. Ozaki and M. Kobayashi: Chem. Lett. 705 (1985);
62. b) N. Kamigata, J. Ozaki and M. Kobayashi: J. Org. Chem. 50 5045 (1985).
63. M. Kameyama, H. Shimezawa, T. Satoh and N. Kamigata: Bull. Chem. Soc. Jpn. 61 1231 (1988).
64. B. M. Culbertson and S. Dietz: J. Chem. Soc. C 992 (1968).
65. a) K. Miura, M. Taniguchi, K. Nozaki, K. Ohshima and K. Utimoto: Tetrahedron Lett. 31 6391 (1990);
66. b) K. Miura, Y. Takeyama, K. Ohshima and K. Utimoto: Bull. Chem. Soc. Jpn. 64 1542 (1991).
67. N. Kamigata, K. Udodaira and T. Shimizu: J. Chem. Soc., Perkin Trans. 1 783 (1997).
68. E. Hirsch, S. Huning and H.-U. Reissing: Chem. Ber. 115 3687 (1982).
69. N. Kamigata, K. Udodaira, M. Yoshikawa and T. Shimizu: J. Organomet. Chem. in press.
70. G. H. Hakimelahi and G. Just: Tetrahedron Lett. 3645 (1979).
71. N. Kamigata, K. Udodaira and T. Shimizu: Phosphorus, Sulfur and Silicon in press.
72. a) H. Nozaki, S. Horiuti, H. Takaya and R. Noyori: Tetrahedron Lett. 5239 (1966);
73. b) T. Aratani: Pure Appl. Chem. 12 1839 (1985).
74. a) M. Kameyama, N. Kamigata and M. Kobayashi: Chem. Lett. 527 (1986);
75. b) M. Kameyama, N. Kamigata and M. Kobayashi: J. Org. Chem. 52 3312 (1987);
76. c) M. Kameyama and N. Kamigata: Bull. Chem. Soc. Jpn. 60 3687 (1987).
77. M. Kameyama and N. Kamigata: Bull. Chem. Soc. Jpn. 62 648 (1989).