Dihaloindium hydride as a novel reducing agent

Chemical Record

Volumn 5, Issue 6, 2005, Pages 323-335

  Baba, Akio ^a   Shibata, Ikuya ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Dehalogenation; Indium hydride; Radical cyclization; Reduction; Reductive aldol reaction

Indexed keywords

EID: 33645529286     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.20055     Document Type: Review

References (117)

1. Barbier-type allylation (a) Araki, S.; Ito, H.; Butsugan, Y. J Org Chem 1988, 53, 1831;
2. (b) Li, C. J.; Chan, T. H. Tetrahedron Lett 1991, 32, 7017;
3. (c) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149;
4. (d) Li, C. J. Tetrahedron Lett 1995, 36, 517;
5. (e) Isaac, M. B.; Chan, T. H. Tetrahedron Lett 1995, 36, 8957;
6. (f) Paquette, L. A.; Mitzel, T. M. J Org Chem 1996, 61, 8799.
7. Pinacol coupling (g) Lim, H. J.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Tetrahedron Lett 1998, 39, 4367.
8. Reduction (h) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028.
9. (a) Ohshita, J.; Schmidbaur, H. J Orgmet Chem 1993, 453, 7;
10. (b) Beachley, O. T., Jr.; Simmons R. D. Inorg Chem 1980, 19, 783;
11. (c) Goode, M. J.; Downs, A. J.; Pulham, C. R.; Rankin, D. W. H.; Robertson H. E. J Chem Soc Chem Commun 1988, 768.
12. Wiberg, E.; Schmidt, M. Z. Naturforsch 1957, 12b, 54.
13. (a) Yamada, M.; Tanaka, K.; Araki, S.; Butsugan, Y. Tetrahedron Lett 1995, 36, 3169;
14. (b) Yamada, M.; Horie, T.; Kawai, M.; Yamamura, H.; Araki, S. Tetrahedron 1997, 53, 15685;
15. (c) Yamada, M.; Tanaka, K.; Butsuga, Y.; Kawai, M.; Yamamura, H.; Araki, S. Main Group Metal Chem 1997, 20, 241.
16. Abernethy, C. D.; Cole, M. L.; Davies, A. J.; C. Jones, Tetrahedron Lett 2000, 41, 7567.
17. Nomura, R.; Miyazaki, S.-I.; Matsuda, H. J Am Chem Soc 1993, 114, 2738.
18. (a) Marshall, J. A.; Hinkle, K. W. J Org Chem 1995, 60, 1920;
19. (b) Marshall, J. A.; Hinkle, K. W. J Org Chem 1996, 61, 105;
20. Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J Org Chem 1991, 56, 2538;
21. (d) Bardot, V.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Synlett 1996, 37;
22. (e) Fujiwara, N.; Yamamoto, Y. J Org Chem 1997, 61, 8799;
23. (f) Araki, S.; Kamei, T.; Hirashita, T.; Yamamura, H.; Kawai, M. Org Lett 2000, 2, 847;
24. (g) Miyai, T.; Inoue, K.; Yasuda, M.; Baba, A. Synlett 1997, 699;
25. (h) Ref [1a].
26. (a) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can J Chem 1994, 72, 1181;
27. (b) Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J Org Chem 1994, 59, 3714;
28. (c) Prenner, R.; Binder, W. H.; Schmid, W. Liebigs Ann Chem 1994, 73;
29. (d) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett 1995, 36, 6863;
30. (e) Chan, T. H.; Issac, M. B. Pure Appl Chem 1996, 68, 919;
31. (f) Li, X.-R.; Loh, T.-P. Tetrahedron Asymm 1996, 7, 1535;
32. (g) Paquette, L. A.; Mitzel, T. M.; Issac, M. B.; Crasto, C. F.; Schomer, W. W. J Org Chem 1997, 62, 4293;
33. (h) Bryan, V. J.; Chan, T. H. Tetrahedron Lett 1997, 38, 6493;
34. (i) Loh, T. P.; Xu, K. C.; Ho, D. S.-C.; Sim, K.-Y. Synlett 1998, 369;
35. (j) Lloyd-Jones, G. C.; Russel, T. Synlett 1998, 903;
36. (k) Loh, T. P.; Wei, L. L. Synlett 1998, 975;
37. Ref [1a].
38. Yasuda, M.; Miyai, T.; Shibata, I.; Nomura, R.; Matsuda, H.; Baba, A. Tetrahedron Lett 1995, 36, 9497.
39. Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett 1998, 39, 1929.
40. For example: (a) Seyferth, D.; Weiner, M. A. J Am Chem Soc 1961, 26, 4797;
41. (b) Milstein, D.; Stille, J. K. J Am Chem Soc 1978, 100, 3636;
42. (c) Kosugi, M.; Shimizu, Y.; Migita, T. Chem Lett 1977, 1423;
43. (d) Keck, G. E.; Abbott, D. E.; Borden, E. P.; Enholm, E. J. Tetrahedron Lett 1984, 25, 3927;
44. (e) Denmark, S. E.; Wilson, T.; Willson, T. M. J Am Chem Soc 1988, 110, 984.
45. (f) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J Org Chem 1994, 59, 5905;
46. (g) Nakamura, H.; Asao, N.; Yamamoto, Y. J Chem Soc Chem Commun 1995, 1273;
47. (h) Yasuda, M.; Sugawa, Y.; Yamamoto, A.; Shibata, I.; Baba, A. Tetrahedron Lett 1996, 37, 5951;
48. Thomas, E. J. Chem Commun 1997, 411;
49. (j) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1992, 49, 7395.
50. Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett 2000, 41, 113.
51. Mosettig, E.; Mozingo, R. Org Reactions 1948, 4, 362.
52. (a) Leblanc, J. C.; Moise, C.; Tirouflet, J. J Organomet Chem 1985, 292, 225;
53. (b) Chatgilialoglu, C.; Lucarini, M. Tetrahedron Lett 1995, 36, 1299;
54. (c) Corriu, R. J. P.; Lanneau, G. F.; Perrot, M. Tetrahedron Lett 1988, 29, 1271;
55. (d) Geng, L.; Lu, X. J Organomet Chem 1989, 379, 41;
56. (e) Malanga, C.; Mannucci, S.; Lardicci, L. Tetrahedron Lett 1997, 38, 8093.
57. (a) Shibata, I.; Kawakami, T.; Tanizawa, D.; Suwa, T.; Sugiyama, E.; Matsuda, H.; Baba, A. J Org Chem 1998, 63, 383;
58. (b) Shibata, I.; Suzuki, T.; Baba, A.; Matsuda, H. J Chem Soc Chem Commun 1988, 882;
59. (c) Shibata, I.; Yoshida, T.; Baba, A.; Matsuda, H. Chem Lett 1991, 307;
60. (d) Kawakami, T.; Shibata, I.; Baba, A.; Matsuda, H. J Org Chem 1993, 58, 7608;
61. (e) Kawakami, T.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. Tetrahedron Lett 1994, 35, 8625;
62. (f) Kawakami, T.; Miyatake, M.; Shibata, I.; Baba, A.; Matsuda, H. J Org Chem 1996, 61, 376.
63. (a) Pereyre, M.; Godet, J. Y. Tetrahedron Lett 1970, 3653;
64. (b) Quintard, J. P.; Pereyre, M. J Organomet Chem 1974, 82, 103.
65. (a) Pereyre, M.; Quintard, P. J.; Rahm, A. Tin in Organic Synthesis; London: Butterworths, 1987.
66. (b) Newmann, W. P. Angew Chem 1963, 225;
67. Fisch, M. H.; Dannenberg, J. J.; Pereyre, M.; Anderson, W. G.; Rens, J.; Grossman, W. E. L. Tetrahedron 1984, 40, 293;
68. (d) Ramaiah, M. Tetrahedron 1987, 43, 3541.
69. Inoue, K.; Ishida, T.; Shibata, I.; Baba, A. Adv Synth Catal 2002, 344, 283.
70. (a) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett 1990, 31, 5331;
71. (b) Enholm, E. J.; Xie, Y.; Abboud, K. A. J Org Chem 1995, 60, 1112;
72. (c) Kawakami, M. T.; Matsuda, H.; Shibata, I.; Miyatake, M.; Suwa, T.; Baba, A. Bull Chem Soc Jpn 1999, 72, 465;
73. (d) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett 1999, 40, 2133;
74. (e) Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A. Tetrahedron Lett 2000, 41, 3403;
75. (f) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J Am Chem Soc 2000, 122, 4528;
76. (g) Ref [15f]
77. (a) Boldrini, G. P.; Mancini, F.; Tagliavini, E.; Trombini, C.; Ronchi, A. U. J Chem Soc Chem Commun 1990, 1680;
78. (b) Boldrini, G. P.; Bortolotti, M.; Mancini, F.; Tagliavini, E.; Trombini, C.; Ronchi, A. U. J Org Chem 1991, 56, 5820.
79. Zimmerman, H. E.; Traxler, M. D. J Am Chem Soc 1957, 79, 1920.
80. anti-Selective aldol reaction which utilized Mg(II) aldolate equilibration has been reported. Swiss, K. A.; Choi, W.-B.; Liotta, D. C.; Abdel-Magid, A. F.; Maryanoff, C. A. J Org Chem 1991, 56, 5978.
81. Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew Chem Int Ed 2004, 43, 711.
82. (a) Greeves, N. N. In Comprehensive Organic Synthesis Vol. 8, B. M. Trost, I. Fleming, Eds. Pergamon Press: Oxford, 1991; p 1.
83. (b) Fry, L.; Orfanopoulos M.; Adlington, M. G.; Dittman, W. R.; Silverman, S. B. J Org Chem 1978, 43, 374.
84. (a) Radicals in Organic Synthesis, Vol. 1-2. P. Renaud, M. P. Sibi, Eds. Wiley-VCH:L Weinheim, 2001.
85. (b) Samir, Z. Z. Radical Reactions in Organic Synthesis; Oxford University Press: Oxford, 2003.
86. (a) Ref [17a];
87. (b) RajanBavu T. V. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7. L. Paquette, Ed. Wiley: New York, 1995; pp 5016-23;
88. Iserloh, H.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417;
89. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995;
90. (e) Smadja, W. Synlett 1994, 1;
91. (f) Sibi, M. P.; Porter, N. A. Acc Chem Res 1999, 32, 153;
92. (g) Renaud, P.; Gerster, M. Angew Chem Int Ed 1998, 37, 2562;
93. (h) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1;
94. Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gurtler, S.; Porter, N. A. J Am Chem Soc 1996, 118, 9200.
95. Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. Tetrahedron Lett 2001, 42, 4661.
96. 3SnH: Menapace, L. W.; Kuivila, H. G. J Am Chem Soc 1964, 86, 3147.
97. 3B; (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull Chem Soc Jpn 1989, 62, 143.
98. 3SnH-9BBN; (b) Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett 1998, 39, 5437.
99. 3SnH-CuCl; (c) Ref [19d].
100. 2; (d) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett 1998, 39, 6335.
101. Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J Am Chem Soc 2002, 124, 906.
102. For reviews see: Studer, A.; Amrein, S. Synthesis 2002, 835.
103. Chatgilialoglu, C. Acc Chem Res 1992, 25, 188.
104. Studer, A.; Amrein, S. Angew Chem Int Ed 2000, 39, 3080.
105. Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415.
106. Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J Am Chem Soc 2001, 123, 3137.
107. Mikami, S.; Fujioka, K.; Nakamura, T.; Yorimitsu, H.; Shinokubo, Y.; Matsubara, S.; Oshima, K. Org Lett 2001, 3, 1853.
108. Banfi, L.; Narisano, F.; Riva, R. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; L. Paquette, Ed. Willey: New York, 1995; p 4522.
109. 4 (1 equiv) and AIBN (0.1 equiv) in diglyme reflux.
110. For the radical clocks studies, Newcomb, N. In Radicals in Organic Synthesis, Vol. 1; P. Renaud, M. P. Sibi, Eds. Willey-VCH: New York, 2001; p 317.
111. Garden, S. J.; Avila, D. V.; Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U.; Lusztyk, J. J Org Chem 1996, 61, 805.
112. Hayashi, N.; Shibata, I.; Baba, A. Org Lett 2004, 6, 4981.
113. Takami, K.; Yorimitsu, H.; Oshima, K. Org Lett 2002, 4, 2993.
114. Banfi, L.; Narisano, E.; Riva, R. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; L Paquette, Ed. Wiley: New York, 1995; p 4522.
115. 3 system must be carried out below -30°C to effect hydroindation as a sole reaction.
116. Hayashi, N.; Shibata, I.; Baba, A. Org Lett 2005, 7, 3093.
117. 3, which may work to decompose substrates or their products. Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Tetrahedron 2002, 58, 8227.