Indium metal and its halides in organic synthesis

European Journal of Organic Chemistry

Volumn , Issue 13, 2000, Pages 2347-2356

  Ranu, Brindaban C ^a,b,c,d,e  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

^b UNIVERSITY OF CALCUTTA   (India)

^c RICE UNIVERSITY   (United States)

^d VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^e UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

Catalysts; Halides; Indium; Organic synthesis

Indexed keywords

ALKYNE; EPOXIDE; HALIDE; INDIUM; PHOSPHONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE;

CATALYST; DEBROMINATION; ESTERIFICATION; REACTION ANALYSIS; REDUCTION; SHORT SURVEY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033928629     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:13<2347::aid-ejoc2347>3.0.co;2-x     Document Type: Short Survey

References (91)

1. H. Gilman, R. G. Jones, J. Am. Chem. Soc. 1940, 62, 2353-2357.
2. Reviews: [2a] P. Cintas, Synlett 1995, 1087-1096. [2b] C.-J. Li, T.-H. Chan, Tetrahedron 1999, 55, 11149-11176.
3. Reviews: [2a] P. Cintas, Synlett 1995, 1087-1096. [2b] C.-J. Li, T.-H. Chan, Tetrahedron 1999, 55, 11149-11176.
4. [3a] X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472-7480 and references therein.
5. [3b] P. C. Lobben, L. A. Paquette, J. Org. Chem. 1998, 63, 6990-6998.
6. [3c] L. A. Paquette, J. L. Mendez-Andino, J. Org. Chem. 1998, 63, 9061-9068.
7. [3d] G. C. L. Jones, T. Russel, Synlett 1998, 903-905.
8. [3e] L. A. Paquette, R. R. Rothhaar, M. Isaac, L. M. Rogers, R. D. Rogers, J. Org. Chem. 1998, 63, 5463-5472.
9. [3f] X.-H. Yi, Y. Meng, C.-J. Li, Chem. Commun. 1998, 449-450.
10. [3g] C. L. Cavallaro, T. Herpin, B. F. McGuinness, Y. C. Shimshock, R. E. Dolle, Tetrahedron Lett. 1999, 40, 2711-2714.
11. [3h] T. Hirashita, T. Kamei, T. Horie, H. Yamamura, M. Kawai, S. Araki, J. Org. Chem. 1999, 64, 172-177.
12. [3i] C.-J. Li, D.-L. Chen, Synlett 1999, 735-736.
13. [4a] I. Perez, J. P. Sestelo, M. A. Maestro, A. Mourino, L. A. Sarandeses, J. Org. Chem. 1998, 63, 10074-10076.
14. [4b] T. H. Chan, W. Lu, Tetrahedron Lett. 1998, 39, 8605-8608.
15. [4c] S. Araki, H. Nakano, K. Subburaj, T. Hirashita, K. Shibutani, H. Yamamura, M. Kawai, Y. Butsugan, Tetrahedron Lett. 1998, 39, 6327-6330.
16. [4d] S. M. Capps, G. C. Lloyd-Jones, M. Murray, T. M. Peakman, K. E. Walsh, Tetrahedron Lett. 1998, 39, 2853-2856.
17. [4e] N. Fujiwara, Y. Yamamoto, Tetrahedron Lett. 1998, 39, 4729-4732.
18. [4f] H. J. Lim, G. Keum, S. B. Kang, Y. Kim, Tetrahedron Lett. 1999, 40, 1547-1550.
19. [4g] S. Araki, T. Horie, M. Kato, T. Hirasuta, H. Yamamura, M. Kawai, Tetrahedron Lett. 1999, 40, 2331-2334.
20. Review: [5a] J. F. Normant, A. Alexis, Synthesis 1981, 841-870. [5b] W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52. [5c] Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
21. Review: [5a] J. F. Normant, A. Alexis, Synthesis 1981, 841-870. [5b] W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52. [5c] Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
22. Review: [5a] J. F. Normant, A. Alexis, Synthesis 1981, 841-870. [5b] W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52. [5c] Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
23. [6a] T. Takahashi, M. Kotora, K. Kasai, N. Suzuki, Tetrahedron Lett. 1994, 35, 5685-5688.
24. [6b] K. Takai, M. Yamada, H. Odaka, K. Utimoto, T. Fujii, I. Furukawa, Chem. Lett. 1995, 315-316.
25. [6c] N. Chatani, N. Amishiro, T. Morii, T. Yamashita, S. Murai, J. Org. Chem. 1995, 60, 1834-1840.
26. [6d] N. Asao, Y. Matsukawa, Y. Yamamoto, Chem. Commun. 1996, 1513-1514.
27. [6e] N. Asao, E. Yoshikawa, Y. Yamamoto, J. Org. Chem. 1996, 61, 4874-4875.
28. S. Araki, A. Imai, K. Shimizu, M. Yamada, A. Mori, Y. Butsugan, J. Org. Chem. 1995, 60, 1841-1847.
29. B. C. Ranu, A. Majee, Chem. Commun. 1997, 1225-1226. A similar allylation of non-functionalized alkynes was reported at the same time by: N. Fujiwara, Y. Yamamoto, J. Org. Chem. 1997, 62, 2318-2319. See also: E. Klaps, W. Schmid, J. Org. Chem. 1999, 64, 7537-7546.
30. B. C. Ranu, A. Majee, Chem. Commun. 1997, 1225-1226. A similar allylation of non-functionalized alkynes was reported at the same time by: N. Fujiwara, Y. Yamamoto, J. Org. Chem. 1997, 62, 2318-2319. See also: E. Klaps, W. Schmid, J. Org. Chem. 1999, 64, 7537-7546.
31. B. C. Ranu, A. Majee, Chem. Commun. 1997, 1225-1226. A similar allylation of non-functionalized alkynes was reported at the same time by: N. Fujiwara, Y. Yamamoto, J. Org. Chem. 1997, 62, 2318-2319. See also: E. Klaps, W. Schmid, J. Org. Chem. 1999, 64, 7537-7546.
32. [9a] E. L. Allred, B. R. Beck, K. J. Voorhees, J. Org. Chem. 1974, 39, 1426-1427.
33. [9b] D. Landini, S. Quici, F. Rolla, Synthesis 1975, 397-399.
34. [9c] D. Savoia, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Org. Chem. 1982, 47, 876-879.
35. [9d] S. G. Davies, S. E. Thomas, Synthesis 1984, 1027-1029.
36. [9e] K. Yamada, R. Yanada, H. Meguri, J. Chem. Soc., Chem. Commun. 1990, 730-732.
37. [9f] J. M. Khurana, G. C. Maikap, J. Org. Chem. 1991, 56, 2582-2584.
38. [9g] R. Yanada, N. Negoro, K. Yanada, T. Fujita, Tetrahedron Lett. 1996, 37, 9313-9316.
39. [9h] C. Malanga, S. Mannucci, L. Lardicci, Tetrahedron 1998, 54, 1021-1028.
40. [9i] T. S. Butcher, M. R. Detty, J. Org. Chem. 1998, 63, 177-180.
41. B. C. Ranu, S. K. Guchhait, A. Sarkar, Chem. Commun. 1998, 2113-2114.
42. T. Hudlicky, G. Sinai-Zingde, M. G. Natchus, Tetrahedron Lett. 1987, 28, 5287-5290.
43. D. C. Billington, Comprehensive Organic Synthesis, vol. 3, chapter 2.11 (Ed.: B. M. Trost), Pergamon, Oxford, 1991.
44. P. E. Fanta, Chem. Rev. 1964, 64, 613-632.
45. V. Penalva, J. Hassan, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron Lett. 1998, 39, 2559-2560.
46. S. Zhang, D. Zhang, L. S. Liebeskind, J. Org. Chem. 1997, 62, 2312-2313 and references therein.
47. [16a] B. C. Ranu, P. Dutta, A. Sarkar, Tetrahedron Lett. 1998, 39, 9557-9558.
48. [16b] S. Araki, T. Shimizu, P. S. Johar, S. J. Jin, Y. Butsugan, J. Org. Chem. 1991, 56, 2538-2542.
49. [16c] S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1991, 64, 727-729.
50. [17a] C. J. Moody, M. R. Pitts, Synlett 1998, 1028-1029.
51. [17b] C. V. Reddy, G. V. Rao, D. S. Iyengar, Tetrahedron Lett. 1999, 40, 3937-3938.
52. B. C. Ranu, P. Dutta, A. Sarkar, J. Chem. Soc., Perkin Trans. 1 1999, 1139-1140.
53. [19a] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1995, 60, 1920-1921 and references therein.
54. [19b] M. Yasuda, T. Miyai, I. Shibata, A. Baba, R. Nomura, H. Maisuda, Tetrahedron Lett. 1995, 36, 9497-9500.
55. [19c] T.-P. Loh, J. Pei, M. Lin, Chem. Commun. 1996, 2315-2316.
56. [19d] G. Babu, P. T. Perumal, Tetrahedron Lett. 1997, 38, 5025-5026.
57. [19e] T.-P. Loh, J. Pei, K. S. Koh, G. Q. Cao, X.-R. Li, Tetrahedron Lett. 1997, 38, 3465-3468.
58. [19f] T.-P. Loh, L. L. Wei, Synlett 1998, 975-976.
59. [19g] T.-P. Loh, K.-C. Xu, D. S. C. Ho, K. Y. Sim, Synlett 1998, 369-370.
60. [19h] T. Miyai, Y. Onishi, A. Baba, Tetrahedron Lett. 1998, 39, 6291-6294.
61. [19i] S. Kobayashi, T. Busujima, S. Nagayama, Tetrahedron Lett. 1998, 39, 1579-1582.
62. [19j] G. Babu, P. T. Perumal, Tetrahedron Lett. 1998, 39, 3225-3228.
63. [19k] T.-P. Loh, L.-L. Wei, Tetrahedron 1998, 7615-7625 and references therein.
64. [19l] J. Yang, C.-J. Li, Synlett 1999, 717-718.
65. [19m] T. Miyai, Y. Onishi, A. Baba, Tetrahedron 1999, 55, 1017-1026.
66. [19n] Y. Yang, G. S. Viswanathan, C.-J. Li, Tetrahedron Lett. 1999, 40, 627-1630.
67. [20a] B. Rickborn, Comprehensive Organic Synthesis, vol. 3, chapter 3 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 733-775.
68. [20b] K. Maruoka, N. Murase, R. Bureau, T. Ooi, H. Yamamoto, Tetrahedron 1994, 50, 3663-3672.
69. [20c] R. Sudha, K. M. Narasimhan, V. G. Saraswathy, S. Sankararaman, J. Org. Chem. 1996, 61, 1877-1879.
70. B. C. Ranu, U. Jana, J. Org. Chem. 1998, 63, 8212-8216.
71. H. O. House, J. Am. Chem. Soc. 1955, 77, 3070-3075.
72. [23a] H. E. Zimmerman L. Singer, B. S. Thyagarajan, J. Am. Chem. Soc. 1959, 81, 108-116.
73. [23b] H. Newman, R. B. Angier, Tetrahedron 1970, 26, 825-836.
74. E. Kienan, K. K. Seth, R. Lamed, J. Am. Chem. Soc. 1986, 108, 3474-3480.
75. S. Laschat, H. Kunz, Synthesis 1992, 90-95.
76. T. Yokomatsu, Y. Yoshida, S. Shibuya, J. Org. Chem. 1994, 59, 7930-7933 and references therein.
77. C. Qian, T. Huang, J. Org. Chem. 1998, 63, 4125-4128.
78. B. C. Ranu, A. Hajra, U. Jana, Org. Lett. 1999, 1, 1141-1143.
79. [29a] C. S. Cho, B. H. Oh, S. C. Shim, Tetrahedron Lett. 1999, 40, 1499-1500.
80. [29b] L. Zhou, Y. Zhang, J. Chem. Soc., Perkin Trans. 1 1998, 2899-2902.
81. [29c] R. C. Larock, M.-Y. Kero, Tetrahedron Lett. 1991, 32, 569-572.
82. [29d] L. Zhou, S.-J. Tu, D.-Q Shi, G.-Y. Dai, W.-X. Chen, Synthesis 1998, 851-854.
83. [29e] R. C. Larock, S. Babu, Tetrahedron Lett. 1987, 28, 5291-5294.
84. [29f] F. Ozawa, H. Yanagihara, A. Yamamoto, J. Org. Chem. 1986, 51, 415-417.
85. [29g] Y. Tsuji, K.-T. Hu, Y. Watanabe, J. Org. Chem. 1987, 52, 1673-1680 and references therein.
86. B. C. Ranu, A. Hajra, U. Jana, Tetrahedron Lett. 2000, 41, 531-533.
87. T.-P. Loh, L.-L. Wei, Synlett 1998, 975-976.
88. [32a] J. Otera, Chem. Rev. 1993, 93, 1449-1470 and references therein.
89. [32b] T. Fujita, M. Tanaka, Y. Norimine, H. Suemune, J. Org. Chem. 1997, 62, 3824-3830.
90. [32c] G. Shapiro, M. Marzi, J. Org. Chem. 1997, 62, 7096-7097.
91. B. C. Ranu, P. Dutta, A. Sarkar, J. Org. Chem. 1998, 63, 6027-6028.