Selenium Compounds as Ligands and Catalysts

Organoselenium Chemistry: Synthesis and Reactions

Volumn , Issue , 2011, Pages 321-360

  Singh, Fateh V ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Darzens reaction; Hydrosilylation; Mizoroki Heck reactions; N iodosuccinimide (NIS); Organoselenium chemistry; Staudinger Vilarrasa reaction

Indexed keywords

EID: 84878041677     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527641949.ch8     Document Type: Chapter

References (147)

1. Huguet, J.L. (1967) Adv. Chem. Ser., 76, 345
2. Jones, D.N., Mundy, D., and Whitehouse, R.D. (1970) J. Chem. Soc., Chem. Commun., 86
3. Walter, R. and Roy, J. (1971) J. Org. Chem., 36, 2561.
4. Wirth, T. (2000) Angew. Chem., 112, 3890
5. Walter, R. and Roy, J. (2000) Angew. Chem., Int. Ed., 39, 3740
6. Freudendahl, D.M., Shahzad, S.A., and Wirth, T. (2009) Eur. J. Org. Chem., 1649
7. Browne, D.M. and Wirth, T. (2006) Curr. Org. Chem., 10, 1893
8. Wirth, T. (1999) Tetrahedron, 55, 1.
9. Santi, C., Santoro, S., and Battistelli, B. (2010) Curr. Org. Chem., 14, 2442
10. Braga, A.L., Lüdtke, D.S., Vargas, F., and Braga, R.C. (2006) Synlett, 1453.
11. Back, T.G. (1999) Organoselenium Chemistry, Oxford University Press, Oxford
12. Wirth, T. (2000) Organoselenium Chemistry: Modern Developments in Organic Synthesis, Top. Curr. Chem., vol. 208, Springer, Berlin
13. Liotta, D. (1987) Organoselenium Chemistry, John Wiley & Sons, Inc., New York
14. Paulmier, C. (1986) Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press, Oxford
15. Patai, S., and Rappoport, Z. (1986). The Chemistry of Organic Selenium and Tellurium Compounds, vol. 1 (eds S. Patai and Z. Rappoport), Wiley, New York.
16. Patai, S. (1987) The Chemistry of Organic Selenium and Tellurium Compounds, vol. 2, Wiley, New York,
17. Nicolaou, K.C. and Petasis, N.A. (1984) Selenium in Natural Products Synthesis, CIS, Philadelphia
18. Krief, A. and Hevesi, L. (1988) Organoselenium Chemistry I, Springer, Berlin
19. Klayman, D.L. and Günther, W.H.H. (1973) Organic Selenium Compounds: Their Chemistry and Biology, Wiley, New York.
20. Beaulieu, P.L. and Déziel, R. (1999) Organoselenium Chemistry: A Practical Approach, (ed. T.G. Back), Oxford University Press, Oxford, pp. 35-66
21. Nishibayashi, Y. and Uemura, S. (2000) Top. Curr. Chem., 208, 201.
22. Mukherjee, A.J., Zade, S.S., Singh, H.B., and Sunoj, R.B. (2010) Chem. Rev., 110, 4357
23. Guillena, G. and Ramon, D.J. (2006) Tetrahedron Asymmetry, 17, 1465
24. Tiecco, M., Testaferri, L., Marini, F., Bagnoli, L., Santi, C., Temperini, A., Sternativo, S., and Tomassini, C. (2005) Phosphorus Sulfur, 180, 729
25. Uemura, S. (1998) Phosphorus Sulfur, 136-138, 219
26. Wessjohann, L.A. and Sinks, U. (1998) J. Prakt. Chem., 340, 189
27. Nishibayashi, Y. and Uemura, S. (1996) Rev. Heteroatom Chem., 14, 83
28. Tiecco, M., Testaferri, L., Tingoli, M., Bagnoli, L., Marini, F., Santi, C., and Temperini, A. (1996) Gazz. Chim. Ital., 126, 635
29. Reich, H.J. and Wollowitz, S. (1993) Org. React., 44, 1
30. Reich, H.J. (1979) Acc. Chem. Res., 12, 22
31. Sharpless, K.B., Gordon, K.M., Lauer, R.F., Patrick, D.W., Sinder, S.P., and Young, M.W. (1975) Chem. Scr., 8A, 9
32. Gosselck, J. (1963) Angew. Chem., 75, 831
33. Gosselck, J. (1963) Angew. Chem., Int. Ed. Engl., 2, 660
34. Petragnani, N., Stefani, H.A., and Valduga, C.J. (2001) Tetrahedron, 57, 1411
35. Tiecco, M. (2000) Top. Curr. Chem., 208, 7
36. McGarrigle, E.M., Myers, E.L., Illa, O., Shaw, M.A., Riches, S.L., and Aggarwal, V.K. (2007) Chem. Rev., 107, 5841.
37. Sonoda, N., Yamamoto, G., Natsukawa, K., Kondo, K., and Murai, S. (1975) Tetrahedron Lett., 24, 1969.
38. Nishibayashi, Y., Singh, J.D., Segawa, K., Fukuzawa, S. -I., and Uemura, S. (1994) J. Chem. Soc., Chem. Commun., 1375.
39. Noyori, R. and Kitamura, M. (1991) Angew. Chem., 103, 34
40. Noyori, R. and Kitamura, M. (1991) Angew. Chem., Int. Ed. Engl., 30, 49.
41. Pu, L. and Yu, H. -B. (2001) Chem. Rev., 101, 757.
42. Wirth, T. (1995) Tetrahedron Lett., 36, 1849
43. Wirth, T., Kulicke, K.J., and Fragale, G. (1996) Helv. Chim. Acta, 79, 1957
44. Santi, C. and Wirth, T. (1999) Tetrahedron Asymmetry, 10, 1019.
45. Braga, A.L., Schneider, P.H., Paixão, M.W., Deobald, A.M., Peppe, C., and Bottega, D.P. (2006) J. Org. Chem., 71, 4305
46. Braga, A.L., Paixão, M.W., Ludtke, D.S., Silveira, C.C., and Rodrigues, O.E.D. (2003) Org. Lett., 5, 2635
47. Braga, A.L., Galetto, F.Z., Rodrigues, O.E.D., Silveira, C.C., and Paixão, M.W. (2008) Chirality, 20, 839.
48. Braga, A.L., Rodrigues, O.E.D., Paixão, M.W., Appelt, H.R., Silveira, C.C., and Bottega, D.P. (2002) Synlett, 2338.
49. Bolm, C., Kesselgruber, M., Grenz, A., Hermanns, N., and Hildebrand, J. (2001) New J. Chem., 25, 13.
50. Schwab, R.S., Soares, L.C., Dornelles, L., Rodrigues, O.E.D., Paixão, M.W., Godoi, M., and Braga, A.L. (2010) Eur. J. Org. Chem., 3574.
51. Nishibayashi, Y., Segawa, K., Singh, J.D., Fukuzawa, S., Ohe, K., and Uemura, S. (1996) Organometallics, 15, 370.
52. Nishibayashi, Y., Singh, J.D., Arikawa, Y., Uemura, S., and Hidai, M. (1997) J. Organomet. Chem., 531, 13.
53. Börner, C., Dennis, M.R., Sinn, E., and Woodward, S. (2001) Eur. J. Org. Chem., 24352.
54. Braga, A.L., Silva, S.J.N., Ludtke, D.S., Drekener, R.L., Silveira, C.C., Rocha, J.B.T., and Wessjohann, L.A. (2002) Tetrahedron Lett., 43, 7329.
55. Shi, M., Wang, C., and Zhang, W. (2004) Chem. Eur. J., 10, 5507.
56. Trost, B.M. and Crawley, M.L. (2003) Chem. Rev., 103, 2921
57. Trost, B.M. and van Vranken, D.L. (1996) Chem. Rev., 96, 395
58. Uenishi, J. and Hamada, M. (2001) Tetrahedron Asymmetry, 12, 2999.
59. Sprinz, J., Kiefer, M., and Helmchen, G. (1994) Tetrahedron Lett., 35, 1523.
60. Hiroi, K., Suzuki, Y., and Abe, I. (1999) Tetrahedron Asymmetry, 10, 1173.
61. You, S. -L., Hou, X. -L., and Dai, L. -X. (2000) Tetrahedron Asymmetry, 11, 1495.
62. Hou, X. -L., Wu, X. -W., Dai, L. -X., Cao, B. -X., and Sun, J. (2000) Chem. Commun., 1195
63. Keehn, P.M., and Rosenfeld, S.M. (1983) Cyclophanes, vol. 71, Academic Press, New York
64. Richards, C.J., Damalidis, T., Hibbs, D.E., and Hursthouse, M.B. (1995) Synlett, 74
65. Sammakia, T. and Latham, H.A. (1995) J. Org. Chem., 60, 6002.
66. Zielinska -B l ajet, M., Siedlecka, R., and Skarzewski, J. (2007) Tetrahedron Asymmetry, 18, 131
67. Sehnem, J.A., Milani, P., Nascimento, V., Andrade, L.H., Dorneles, L., and Braga, A.L. (2010) Tetrahedron Asymmetry, 21, 997.
68. Braga, A.L., Paixão, M.W., and Marin, G. (2005) Synlett, 1975.
69. Vargas, F., Sehnem, J.A., Galetto, F.Z., and Braga, A.L. (2008) Tetrahedron, 64, 392.
70. Yao, Q., Kinney, E.P., and Zheng, C. (2004) Org. Lett., 6, 2997.
71. Mingzhong, C., Jun, Z., Hong, Z., and Caisheng, S. (2002) React. Func. Polym., 50, 191.
72. Cai, M., Liu, G., and Zhou, J. (2005) J. Mol. Catal. A, 227, 107.
73. Jones, R.C., Canty, A.J., Gardiner, M.G., Skelton, B.W., Tolhurst, V. -A., and White, A.H. (2010) Inorg. Chim. Acta, 363, 77.
74. Das, D., Rao, G.K., and Singh, A.K. (2009) Organometallics, 28, 6054.
75. Wallner, O.L. and Szabo, K.J. (2005) J. Org. Chem., 70, 9215.
76. Sebelius, S., Olsson, V.J., and Szabo, K.J. (2005) J. Am. Chem. Soc., 127, 10478.
77. Aydin, J., Selander, N., and Szabo, K.J. (2006) Tetrahedron Lett., 47, 8999.
78. Yao, Q. and Sheets, M. (2006) J. Org. Chem., 71, 5384.
79. Aydin, J., Kumar, K.S., Eriksson, L., and Szab ó, K.J. (2007) Adv. Synth. Catal., 349, 2585.
80. Nishibayashi, Y., Imajima, H., Onodera, G., Hidai, M., and Uemura, S. (2004) Organometallics, 23, 26.
81. Nishibayashi, Y., Imajima, H., Onodera, G., Inada, Y., Hidai, M., and Uemura, S. (2004) Organometallics, 23, 5100.
82. Dochnahl, M., Lohnwitz, K., Luhl, A., Pissarek, J. -W., Biyikal, M., Roesky, P.W., and Blechert, S. (2010) Organometallics, 29, 2637.
83. Schwab, R.S., Galetto, F.Z., Azeredo, J.B., Braga, A.L., Lüdtke, D.S., and Paixão, M.W. (2008) Tetrahedron Lett., 49, 5094.
84. Watanabe, S., Hasebe, R., Ouchi, J., Nagasawa, H., and Kataoka, T. (2010) Tetrahedron Lett., 51, 5778.
85. Miyata, T., Kondo, K., Murai, S., Hirashima, T., and Sonoda, N. (1980) Angew. Chem., 92, 1040
86. Miyata, T., Kondo, K., Murai, S., Hirashima, T., and Sonoda, N. (1980) Angew. Chem., Int. Ed. Engl., 19, 1008.
87. Liu, X. -Z. and Lu, S. -W. (2003) Chem. Lett., 32, 1142.
88. Wang, X., Lu, S., and Yu, Z. (2004) Adv. Synth. Catal., 346, 929.
89. Wang, X., Li, P., Yuan, X., and Lu, S. (2006) J. Mol. Catal. A, 253, 261.
90. Wang, X., Ling, G., Xue, Y., and Lu, S. (2005) Eur. J. Org. Chem., 1675.
91. Tian, F. and Lu, S. (2004) Synlett, 1953.
92. Hori, T. and Sharpless, K.B. (1979) J. Org. Chem., 44, 4204.
93. Tunge, J.A. and Mellegaard, S.R. (2004) Org. Lett., 6, 1205.
94. Barrero, A.F., Quílez del Moral, J.F., Herrador, M.M., Cortés, M., Arteaga, P., Catalán, J.V., Sánchez, E.M., and Arteaga, J.F. (2006) J. Org. Chem., 71, 5811.
95. Mellegaard, S.R. and Tunge, J.A. (2004) J. Org. Chem., 69, 8979.
96. Bures, J., Martin, M., Urpi, F., and Vilarrasa, J. (2009) J. Org. Chem., 74, 2203.
97. Crich, D., Neelamkavil, S., and Sartillo -Piscil, F. (2000) Org. Lett., 2, 4029.
98. Ford, L., Wille, U., and Schiesser, C.H. (2006) Helv. Chim. Acta, 89, 2306.
99. Crich, D., Hao, X., and Lucas, M. (1999) Tetrahedron, 53, 14261.
100. Pandey, G., Rao, K.S.S.P., and Rao, K.V.N. (2000) J. Org. Chem., 65, 4309.
101. Clive, D.L.J., Pham, M.P., and Subedi, R. (2007) J. Am. Chem. Soc., 129, 2713.
102. Crich, D. and Sannigrahi, M. (2002) Tetrahedron, 58, 3319.
103. Crich, D. and Rumthao, S. (2004) Tetrahedron, 60, 1513.
104. Crich, D. and Patel, M. (2005) Org. Lett., 7, 3625.
105. Barton, D.H.R., Brewster, A.G., Hui, A.H.F., Lester, D.J., Ley, S.V., and Back, T.G. (1978) J. Chem. Soc., Chem. Commun., 952.
106. Umbreit, M.A. and Sharpless, K.B. (1977) J. Am. Chem. Soc., 99, 5526.
107. Taylor, R.T. and Flood, L.A. (1983) J. Org. Chem., 48, 5160.
108. Sharpless, K.B. and Young, M.W. (1975) J. Org. Chem., 40, 947.
109. Hori, T. and Sharpless, K.B. (1978) J. Org. Chem., 43, 1689.
110. Betzemeier, B., Lhermitte, F., and Knochel, P. (1999) Synlett, 489.
111. Goodman, M.A. and Detty, M.R. (2006) Synlett, 1100.
112. Garcia -Marin, H., van der Toorn, J.C., Mayoral, J.A., Garcia, J.I., and Arends, I.W.C.E. (2009) Green Chem., 11, 1605.
113. Syper, L. and Mlochowski, J. (1984) Synthesis, 747.
114. Syper, L. and Mlochowski, J. (1987) Tetrahedron, 43, 207.
115. Gogoi, P., Sharma, S.D., and Konwar, D. (2007) Lett. Org. Chem., 4, 249.
116. Santoro, S., Santi, C., Sabatini, M., Testaferri, L., and Tiecco, M. (2008) Adv. Synth. Catal., 350, 2881.
117. Brodsky, B.H. and Bois, J.D. (2005) J. Am. Chem. Soc., 127, 15391.
118. Carrera, I., Brovetto, M.C., and Seoane, G.A. (2006) Tetrahedron Lett., 47, 7849.
119. Backvall, J. -E. (2004) Modern Oxidation Methods, Wiley, New York.
120. Onami, T., Ikeda, M., and Woodard, S.S. (1996) Bull. Chem. Soc. Jpn., 69, 3601.
121. Ehara, H., Noguchi, M., Sayama, S., and Onami, T. (2000) J. Chem. Soc., Perkin Trans. 1, 1429.
122. van der Toorn, J.C., Kemperman, G., Sheldon, R.A., and Arends, I.W.C.E. (2009) J. Org. Chem., 74, 3085.
123. Singh, P., and Singh, A.K. (2010) Eur. J. Inorg. Chem., 4187.
124. Brink, G., Vis, J. -M., Arends, I.W.C.E., and Sheldon, R.A. (2001) J. Org. Chem., 66, 2429.
125. Miyake, Y., Nishibayashi, Y., and Uemura, S. (2002) Bull. Chem. Soc. Jpn., 75, 2233.
126. Ichikawa, H., Usami, Y., and Arimoto, M. (2005) Tetrahedron Lett., 46, 8665.
127. Wójtowicz, H., Brzaszcz, M., Kloc, K., and Mlochowski, J. (2001) Tetrahedron, 57, 9743.
128. Crich, D. and Zou, Y. (2004) Org. Lett., 6, 775.
129. Crich, D. and Zou, Y. (2005) J. Org. Chem., 70, 3309.
130. Zhao, D., Johansson, M., and Bäckvall, J. -E. (2007) Eur. J. Org. Chem., 4431.
131. Gebhardt, C., Priewisch, B., Irran, E., and Rück -Braun, K. (2008) Synthesis, 1889.
132. Santoro, S., Battistelli, B., Gjoka, B., Si, C. -W.S., Testaferri, L., Tiecco, M., and Santi, C. (2010) Synlett, 1402.
133. Drake, M.D., Bateman, M.A., and Detty, M.R. (2003) Organometallics, 22, 4158.
134. Goodman, M.A. and Detty, M.R. (2004) Organometallics, 23, 3016.
135. Francavilla, C., Drake, M.D., Bright, F.V., and Detty, M.R. (2001) J. Am. Chem. Soc., 123, 57.
136. Drake, M.D., Bright, F.V., and Detty, M.R. (2003) J. Am. Chem. Soc., 125, 12558.
137. Bennett, S.M., Tang, Y., McMaster, D., Bright, F.V., and Detty, M.R. (2008) J. Org. Chem., 73, 6849.
138. Mellegaard -Waetzig, S.R., Wang, C., and Tunge, J.A. (2006) Tetrahedron, 62, 7191.
139. Wirth, T., Häuptli, S., and Leuenberger, M. (1998) Tetrahedron Asymmetry, 9, 547
140. Browne, D.M., Niyomura, O. and Wirth, T. (2008) Phosphorus Sulfur, 183, 1026.
141. Browne, D.M., Niyomura, O., and Wirth, T. (2007) Org. Lett., 9, 3169
142. Freudendahl, D.M., Santoro, S., Shahzad, S.A., Santi, C., and Wirth, T. (2009) Angew. Chem., 121, 8559
143. Freudendahl, D.M., Santoro, S., Shahzad, S.A., Santi, C., and Wirth, T. (2009) Angew. Chem., Int. Ed., 48, 8409.
144. Shahzad, S.A., Venin, C., and Wirth, T. (2010) Eur. J. Org. Chem., 465.
145. Lenardao, E.J., Mendes, S.R., Ferreira, P.C., Perin, G., Silveira, C.C., and Jacob, R.G. (2006) Tetrahedron Lett., 47, 7439.
146. Lenardao, E.J., Borges, E.L., Mendes, S.R., Perin, G., and Jacob, R.G. (2008) Tetrahedron Lett., 49, 1919.
147. Lenardao, E.J., Feijo, J.O., Thurow, S., Perin, G., Jacob, R.G., and Silveira, C.C. (2009) Tetrahedron Lett., 50, 5215.