1,3-Dipolar cycloaddition of nitrone-type dipoles to uncomplexed and metal-bound substrates bearing the C{triple bond, long}N triple bond

Coordination Chemistry Reviews

Volumn 255, Issue 23-24, 2011, Pages 2946-2967

  Bokach, Nadezhda A ^a   Kuznetsov, Maxim L ^b   Kukushkin, Vadim Yu ^a,c  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

Author keywords

1,3 Dipolar cycloaddition; 2,3 Dihydro 1,2,4 oxadiazoles; Aminocarbenes; Isocyanide ligands; Ligand reactivity; Nitrile ligands; Nitrones

Indexed keywords

EID: 80055063960     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2011.07.001     Document Type: Review

References (127)

1. Broggini G., Molteni G., Terraneo A., Zecchi G. Heterocycles 2003, 59:823.
2. Cycloaddition Reactions in Organic Synthesis 2001, Wiley-VCH Verlag GmbH. S. Kobayashi, K.A. Jørgensen (Eds.).
3. Kukushkin V.Yu., Pombeiro A.J.L. Chem. Rev. 2002, 102:1771.
4. Gothelf K.V., Jørgensen K.A. Chem. Commun. 2000, 1449.
5. Gothelf K.V., Jørgensen K.A. Chem. Rev. 1998, 98:863.
6. Lautens M., Klute W., Tam W. Chem. Rev. 1996, 96:49.
7. Alvarez-Corral M., Muñoz-Dorado M., Rodríguez-García I. Chem. Rev. 2008, 108:3174.
8. Appukkuttan P., Mehta V.P., van der Eycken E.V. Chem. Soc. Rev. 2010, 39:1467.
9. Becer C.R., Hoogenboom R., Schubert U.S. Angew. Chem. Int. Ed. 2009, 48:4900.
10. Hein J.E., Fokin V.V. Chem. Soc. Rev. 2010, 39:1302.
11. Kappe C.O., van der Eycken E. Chem. Soc. Rev. 2010, 39:1280.
12. Meldal M., Tornøe C.W. Chem. Rev. 2008, 108:2952.
13. Naodovic M., Yamamoto H. Chem. Rev. 2008, 108:3132.
14. Partyka D.V., Gao L., Teets T.S., Updegraff J.B., Deligonul N., Gray T.G. Organometallics 2009, 28:6171.
15. Pellissier H. Tetrahedron 2007, 63:3235.
16. Najera C., Sansano J., Yus M. J. Braz. Chem. Soc. 2010, 21:377.
17. Zhang X.-M. Coord. Chem. Rev. 2005, 249:1201.
18. Ostrovskii V.A., Koldobskii G.I., Trifonov R.E. Comprehensive Heterocyclic Chemistry III 2009, vol. 6:257. Elsevier, Oxford.
19. Zhao H., Qu Z.R., Ye H.Y., Xiong R.G. Chem. Soc. Rev. 2008, 37:84.
20. Bosch L., Vilarrasa J. Angew. Chem. Int. Ed. 2007, 46:3926.
21. Lutz J.-F. Angew. Chem. Int. Ed. 2007, 46:1018.
22. Nair V., Suja T.D. Tetrahedron 2007, 63:12247.
23. Li Z., Li M., Zhou X.P., Wu T., Li D., Ng S.W. Cryst. Growth Des. 2007, 7:1992.
24. Aureggi V., Sedelmeier G. Angew. Chem. Int. Ed. 2007, 46:8440.
25. Aldhoun M., Massi A., Dondoni A. J. Org. Chem. 2008, 73:9565.
26. Bonnamour J., Bolm C. Chem. Eur. J. 2009, 15:4543.
27. Nasrollahzadeh M., Habibi D., Shahkarami Z., Bayat Y. Tetrahedron 2009, 65:10715.
28. Habibi D., Nasrollahzadeh M., Faraji A.R., Bayat Y. Tetrahedron 2010, 66:3866.
29. Huang X., Li P., Li X.-S., Xu D.-C., Xie J.-W. Org. Biomol. Chem. 2010, 4527.
30. Gutmann B., Roduit J.-P., Roberge D., Kappe C.O. Angew. Chem. Int. Ed. 2010, 49:7101.
31. Bokach N.A., Khripoun A.V., Kukushkin V.Y. Inorg. Chem. 2003, 42:896.
32. Bokach N.A., Kukushkin V.Y., Haukka M. Eur. J. Inorg. Chem. 2005, 845.
33. Pineiro M., Pinho e Melo T.M.V.D. Eur. J. Org. Chem. 2009, 2009:5287.
34. Kim Y.J., Chang X.H., Han J.T., Lim M.S., Lee S.W. Dalton Trans. 2004, 3699.
35. Kim Y.J., Kwak Y.S., Joo Y.S., Lee S.W. J. Chem. Soc., Dalton Trans. 2002, 144.
36. Kim Y.J., Lee K.E., Jeon H.T., Huh H.S., Lee S.W. Inorg. Chim. Acta 2008, 361:2159.
37. Huh H.S., Lee Y.K., Lee S.W. J. Mol. Struct. 2006, 789:209.
38. Fuchita Y., Hidaka K., Morinaga S., Hiraki K. Bull. Chem. Soc. Jpn. 1981, 54:800.
39. Luzyanin K.V., Tskhovrebov A.G., Guedes da Silva M.F.C., Haukka M., Pombeiro A.J.L., Kukushkin V.Y. Chem. Eur. J. 2009, 15:5969.
40. Bokach N.A., Kukushkin V.Y. Russ. Chem. Bull. 2006, 55:1869.
41. Bokach N.A. Russ. Chem. Rev. 2010, 79:89.
42. Bokach N.A., Ioffe S.L., Dolgushin F.M., Antipin M.Y., Tartakovskii V.A., Kukushkin V.Y. Inorg. Chem. Commun. 2009, 12:173.
43. Eberson L., McCullough J.J., Hartshorn C.M., Hartshorn M.P. J. Chem. Soc., Perkin Trans. 1998, 2:41.
44. Sang H., Janzen E.G., Poyer J.L. J. Chem. Soc., Perkin Trans. 1996, 2:1183.
45. Padwa A., Kline D.N., Koehler K.F., Matzinger M., Venkatramanan M.K. J. Org. Chem. 1987, 52:3909.
46. Plate R., Hermkens P.H.H., Smits J.M.M., Nivard R.J.F., Ottenheijm H.C.J. J. Org. Chem. 1987, 52:1047.
47. Hermkens P.H.H., Maarseveen J.H.v., Kruse C.G., Scheeren H.W. Tetrahedron 1988, 44:6491.
48. Diaz-Ortiz A., Diez-Barra E., de la Hoz A., Moreno A., Gómez-Escalonilla M.J., Loupy A. Heterocycles 1996, 43:1021.
49. Wagner G., Garland T. Tetrahedron Lett. 2008, 49:3596.
50. Yu Y., Fujita H., Ohno M., Eguchi S. Synthesis 1995, 498.
51. Yu Y., Watanabe N., Ohno M., Eguchi S. J. Chem. Soc., Perkin Trans. 1995, 1:1417.
52. Lasri J., Kopylovich M.N., Guedes da Silva M.F.C., Charmier M.A.J., Pombeiro A.J.L. Chem. Eur. J. 2008, 14:9312.
53. Kuznetsov M.L., Kukushkin V.Y. J. Org. Chem. 2006, 71:582.
54. Kuznetsov M.L., Kukushkin V.Y., Dement'ev A.I., Pombeiro A.J.L. J. Phys. Chem. A 2003, 107:6108.
55. Wagner G. Chem. Eur. J. 2003, 9:1503.
56. Yu Y., Ohno M., Eguchi S. J. Chem. Soc., Chem. Commun. 1994, 331.
57. Torssell K.B.G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis (Organic Nitro Chemistry) 1988, Wiley-VCH, Weinheim.
58. Bokach N.A., Kuznetsov M.L., Haukka M., Ovcharenko V.I., Tretyakov E.V., Kukushkin V.Y. Organometallics 2009, 28:1406.
59. Kuznetsov M.L., Nazarov A.A., Kozlova L.V., Kukushkin V.Y. J. Org. Chem. 2007, 72:4475.
60. Charmier M.A.J., Kukushkin V.Y., Pombeiro A.J.L. J. Chem. Soc., Dalton Trans. 2003, 2540.
61. Troisi L., Ronzini L., Rosato F., Videtta V. Synlett 2009, 1806.
62. Troisi L., Rosato F., Caccamese S., Videtta V., Pilati T. Synthesis 2010, 3211.
63. Wagner G., Haukka M., Fraústo da Silva J.J.R., Pombeiro A.J.L., Kukushkin V.Y. Inorg. Chem. 2001, 40:264.
64. Wagner G., Pombeiro A.J.L., Kukushkin V.Y. J. Am. Chem. Soc. 2000, 122:3106.
65. Sustmann R. Tetrahedron Lett. 1971, 12:2717.
66. Sustmann R. Tetrahedron Lett. 1971, 12:2721.
67. Kuznetsov M.L. Russ. Chem. Rev. 2006, 75:935.
68. Kuznetsov M.L. Uspekhi Khimii 2006, 75:1045.
69. Kuznetsov M.L. J. Mol. Struct., Theochem. 2004, 674:33.
70. Kuznetsov M.L., Kukushkin V.Y., Pombeiro A.J.L. Dalton Trans. 2008, 1312.
71. Kuznetsov M.L., Kukushkin V.Y., Pombeiro A.J.L. J. Org. Chem. 2010, 75:1474.
72. Kuznetsov M.L., Kozlova L.V., Dement'ev A.I. Russ. J. Inorg. Chem. 2006, 51:1602.
73. Wagner G., Danks T.N., Desai B. Tetrahedron 2008, 64:477.
74. Charmier M.A.J., Haukka M., Pombeiro A.J.L. Dalton Trans. 2004, 2741.
75. Moyano A., Pericàs M.A., Valentí E. J. Org. Chem. 1989, 54:573.
76. Lecea B., Arrieta A., Roa G., Ugalde J.M., Cossío F.P. J. Am. Chem. Soc. 1994, 116:9613.
77. Morao I., Lecea B., Cossío F.P. J. Org. Chem. 1997, 62:7033.
78. Cossío F.P., Morao I., Jiao H., Schleyer P.v.R. J. Am. Chem. Soc. 1999, 121:6737.
79. Wagner G. Inorg. Chim. Acta 2004, 357:1320.
80. Pearson R.G., Songstad J. J. Am. Chem. Soc. 2002, 89:1827.
81. Woodward S. Tetrahedron 2002, 58:1017.
82. Bokach N.A., Krokhin A.A., Nazarov A.A., Kukushkin V.Y., Haukka M., Fraústo da Silva J.J.R., Pombeiro A.J.L. Eur. J. Inorg. Chem. 2005, 3042.
83. Lasri J., Charmier M.A.J., Haukka M., Pombeiro A.J.L. J. Org. Chem. 2007, 72:750.
84. Kritchenkov A.S., Bokach N.A., Haukka M., Kukushkin V.Y. Dalton Trans. 2011, 40:4175.
85. Desai B., Danks T.N., Wagner G. Dalton Trans. 2004, 166.
86. Lasri J., Guedes da Silva M.F.C., Kopylovich M.N., Mukhopadhyay S., Charmier M.A.J., Pombeiro A.J.L. Dalton Trans. 2009, 2210.
87. Makarycheva-Mikhailova A.V., Golenetskaya J.A., Bokach N.A., Balova I.A., Haukka M., Kukushkin V.Y. Inorg. Chem. 2007, 46:8323.
88. Kappe C.O. Angew. Chem. Int. Ed. 2004, 43:6250.
89. Kappe C.O., Dallinger D. Mol. Divers. 2009, 13:71.
90. Kranjc K., Kocevar M. Curr. Org. Chem. 2010, 14:1050.
91. de la Hoz A., Diaz-Ortiz A., Moreno A., Sanchez-Migallon A., Prieto P., Carrillo J.R., Vazquez E., Gomez M.V., Herrero M.A. Comb. Chem. High Throughput Screen. 2007, 10:877.
92. Desai B., Danks T.N., Wagner G. J. Chem. Soc., Dalton Trans. 2003, 2544.
93. Tagawa Y., Honjo N., Goto Y., Kato T. Chem. Pharm. Bull. 1986, 34:4984.
94. Chiang Y.H. J. Org. Chem. 1971, 36:2146.
95. Mukaiyama T., Hoshino T. J. Am. Chem. Soc. 1960, 82:5339.
96. Patel S.B., Patel M.R., Mankad B.N. Indian J. Chem. 1967, 5:545.
97. Kroehnke B. Chem. Ber. 1936, 69:2006.
98. Sharma S.D., Gogoi P., Konwar D. Indian J. Chem., Sect. B 2007, 46:1672.
99. Liu M.-Ch., Lin T.-Sh., Penketh P., Sartorelli A.C. J. Med. Chem. 1995, 38:4234.
100. Kozhevnikov D.N., Kovalev I.S., Prokhorov A.M., Rusinov V.L., Chupakhin O.N. Russ. Chem. Bull. 2003, 52:1588.
101. Klicnar J., Toman J., Lycka A., Hasek J., Jecny J., Huml K. J. Chem. Soc., Perkin Trans. 1990, 1:3049.
102. Greenhill J.V., Loghmani-Khouzani H., Maitland D.J. J. Chem. Soc., Perkin Trans. 1991, 1:2831.
103. Funakoshi K., Inada H., Hamana M. Chem. Pharm. Bull. 1984, 32:4731.
104. Wagner G., Haukka M. J. Chem. Soc., Dalton Trans. 2001, 2690.
105. Bokach N.A., Balova I.A., Haukka M., Kukushkin V.Y. Organometallics 2011, 30:595.
106. V.Y. Kukushkin, A.J.L. Pombeiro, J.J.R. Fraústo da Silva, G. Wagner, Patent WO 0198283, 2001; Chem. Abstr. 136 (2001) 53750.
107. Pavez H., Marquez A., Navarrette P., Tzichinovsky S., Rodriguez H. Tetrahedron 1987, 43:2223.
108. Farrell N. Met. Ions Biol. Syst. 1996, 32:603.
109. Arandjelovic S., Tesic Z., Radulovic S. Med. Chem. Rev. 2005, 2:415.
110. Coluccia M., Natile G. Anti-Cancer Agents Med. Chem. 2007, 7:111.
111. Kalinowska-Lis U., Ochocki J., Matlawska-Wasowska K. Coord. Chem. Rev. 2008, 252:1328.
112. Aris S.M., Farrell N.P. Eur. J. Inorg. Chem. 2009, 1293.
113. Cossa G., Gatti L., Zunino F., Perego P. Curr. Med. Chem. 2009, 16:2355.
114. Coley H.M., Sarju J., Wagner G. J. Med. Chem. 2008, 51:135.
115. Wagner G., Marchant A., Sayer J. Dalton Trans. 2010, 39:7747.
116. Luzyanin K.V., Tskhovrebov A.G., Carias M.C., Guedes da Silva M.F.C., Pombeiro A.J.L., Kukushkin V.Y. Organometallics 2009, 28:6559.
117. Menezes F.M., Kuznetsov M.L., Pombeiro A.J.L. Organometallics 2009, 28:6593.
118. Hahn F.E., Jahnke M.C. Angew. Chem. Int. Ed. 2008, 47:3122.
119. Frémont P., Marion N., Nolan S.P. Coord. Chem. Rev. 2009, 253:862.
120. Luzyanin K.V., Pombeiro A.J.L., Haukka M., Kukushkin V.Y. Organometallics 2008, 27:5379.
121. Luzyanin K.V., Guedes da Silva M.F.C., Kukushkin V.Y., Pombeiro A.J.L. Inorg. Chim. Acta 2009, 362:833.
122. Tskhovrebov A.G., Luzyanin K.V., Kuznetsov M.L., Sorokoumov V.N., Balova I.A., Haukka M., Kukushkin V.Y. Organometallics 2011, 30:3362.
123. Slaughter L.M. Comments Inorg. Chem. 2008, 29:46.
124. Dhudshia B., Thadani A.N. Chem. Commun. 2006, 6:668.
125. Moncada A.I., Manne S., Tanski J.M., Slaughter L.M. Organometallics 2006, 25:491.
126. Moncada A.I., Khanb M.A., Slaughter L.M. Tetrahedron Lett. 2005, 46:1399.
127. Kremzow D., Seidel G., Lehmann C.W., Furstner A. Chem. Eur. J. 2005, 11:1833.