Connection of metallamacrocycles via dynamic covalent chemistry: A versatile method for the synthesis of molecular cages

Journal of the American Chemical Society

Volumn 133, Issue 18, 2011, Pages 7106-7115

  Granzhan, Anton ^a   Schouwey, Clément ^a   Riis Johannessen, Thomas ^a   Scopelliti, Rosario ^a   Severin, Kay ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2-PYRIDONES; CAGE STRUCTURES; CAVITY SIZE; CHEMOSELECTIVE; DIASTEREOSELECTIVE; DYNAMIC COVALENT CHEMISTRY; ETHYLENE DIAMINE; EXCHANGE PROCESS; METALLAMACROCYCLES; MODULAR APPROACH; ONE-POT REACTION; P-CYMENE; PYRIDONES; SELF-SORTING; TRIAMINES; VERSATILE METHODS;

ALDEHYDES; LIGANDS; ORGANIC COMPOUNDS; RUTHENIUM COMPOUNDS; X RAY CRYSTALLOGRAPHY;

CONDENSATION REACTIONS;

ALDEHYDE; BENZENE DERIVATIVE; DIPYRONE; ETHYLENEDIAMINE; LIGAND; MACROCYCLIC COMPOUND; METALLAMACROCYCLIC COMPOUND; PARA CYMENE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; MOLECULAR DYNAMICS; ONE POT SYNTHESIS; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; CHLORIDES; CRYSTALLOGRAPHY, X-RAY; LIGANDS; MACROCYCLIC COMPOUNDS; MONOTERPENES; ORGANOMETALLIC COMPOUNDS; PYRIDINES; RUBIDIUM;

EID: 79955685847     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200580x     Document Type: Article

References (147)

1. (a) Sitharam, M.; Agbandje-McKenna, M. J. Comput. Biol. 2006, 13, 1232-1265.
2. (b) Zlotnick, A. J. Mol. Recognit. 2005, 18, 479-490.
3. (c) Zlotnick, A.; Stray, S. J. Trends Biotechnol. 2003, 21, 536-542.
4. (a) Harrison, P. M.; Arosio, P. Biochim. Biophys. Acta, Bioenerg. 1996, 1275, 161-203.
5. (b) Gerl, M.; Jaenicke, R. Eur. Biophys. J. 1987, 15, 103-109.
6. (c) Gerl, M.; Jaenicke, R. Biochemistry 1988, 27, 4089-4096.
7. Mastlerz, M. Angew. Chem. Int. Ed. 2010, 49, 5042-5053.
8. (a) Scarso, A.; Rebek, J., Jr. Top. Curr. Chem. 2006, 265, 1-46.
9. (b) Müller, A.; Roy, S. J. Mater. Chem. 2005, 15, 4673-4677.
10. (c) Johnston, M. R.; Latter, M. J. Supramol. Chem. 2005, 17, 595-607.
11. (d) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem. Int. Ed. 2002, 41, 1488-1508.
12. (a) Jin, P.; Dalgarno, S. J.; Atwood, J. L. Coord. Chem. Rev. 2010, 254, 1760-1768.
13. (b) Ward, M. D. Chem. Commun. 2009, 4487-4499.
14. (c) Therrien, B. Eur. J. Inorg. Chem. 2009, 2445-2453.
15. (d) Han, Y.-F.; Jia, W.-G.; Yu, W.-B.; Jin, G.-X. Chem. Soc. Rev. 2009, 38, 3419-3434.
16. (e) Saalfrank, R. W.; Maid, H.; Scheurer, A. Angew. Chem. Int. Ed. 2008, 47, 8794-8824.
17. (f) Tranchemontagne, D. J.; Ni, Z.; O'Keeffe, M.; Yaghi, O. M. Angew. Chem. Int. Ed. 2008, 47, 5136-5147.
18. (g) Dalgarno, S. J.; Power, N. P.; Atwood, J. L. Coord. Chem. Rev. 2008, 252, 825-841.
19. (h) Schmittel, M.; Kalsani, V. Top. Curr. Chem. 2005, 245, 1-53.
20. (i) Maurizot, V.; Yoshizawa, M.; Kawano, M.; Fujita, M. Dalton Trans. 2006, 2750-2756.
21. (j) Hamilton, T. D.; MayGillivray, L. R. Cryst. Growth Des. 2004, 4, 419-430.
22. (k) Seidel, S. R.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983.
23. (l) Wang, M.; Zheng, Y.-R.; Ghosh, K.; Stang, P. J. J. Am. Chem. Soc. 2010, 132, 6282-6283.
24. (m) Bar, A. K.; Mostafa, G.; Mukherjee, P. S. Inorg. Chem. 2010, 49, 7647-7649.
25. (n) Bar, A. K.; Chakrabarty, R.; Mostafa, G.; Mukherjee, P. S. Angew. Chem. Int. Ed. 2008, 47, 8455-8459.
26. (a) Wiester, M. J.; Ulmann, P. A.; Mirkin, C. A. Angew. Chem. Int. Ed. 2011, 50, 114-137.
27. (b) Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Angew. Chem. Int. Ed. 2009, 48, 3418-3438.
28. (c) Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2009, 42, 1650-1659.
29. (d) Koblenz, T. S.; Wassenaar, J.; Reek, J. N. H. Chem. Soc. Rev. 2008, 37, 247-262.
30. (e) Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 349-358.
31. (a) Zava, O.; Mattsson, J.; Therrien, B.; Dyson, P. J. Chem. Eur. J. 2010, 16, 1428-1431.
32. (b) Therrien, B.; Süss-Fink, G.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J. Angew. Chem. Int. Ed. 2008, 47, 3773-3776.
33. (a) Breiner, B.; Clegg, J. K.; Nitschke, J. R. Chem. Sci. 2011, 2, 51-56.
34. (b) Rebek, J., Jr. Nature 2006, 444, 557.
35. Review: (a) Klosterman, J. K.; Yamauchi, Y.; Fujita, M. Chem. Soc. Rev. 2009, 38, 1714-1725.
36. For recent examples see: (1) (b) Yamauchi, Y.; Hanaoka, Y.; Yoshizawa, M.; Akita, M.; Ichikawa, T.; Yoshio, M.; Kato, T.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 9555-9557.
37. (c) Murase, T.; Otsuka, K.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 7864-7865.
38. (d) Osuga, T.; Murase, T.; Ono, K.; Yamauchi, Y.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 15553-15555.
39. For selected examples see: (a) Atwood, J. L.; Szumna, A. J. Am. Chem. Soc. 2002, 124, 10646-10647.
40. (b) Atwood, J. L.; Barbour, L. J.; Jerga, A. Chem. Commun. 2001, 2376-2377.
41. (c) Prins, L. J.; De Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184.
42. (d) Klok, H.-A.; Jolliffe, K. A.; Schauer, C. L.; Prins, L. J.; Spatz, J. P.; Möller, M.; Timmerman, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1999, 121, 7154-7155.
43. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. Science 1998, 279, 1021-1023.
44. (f) Martín, T.; Obst, U.; Rebek, J., Jr. Science 1998, 281, 1842-1845.
45. (g) Timmerman, P.; Vreekamp, R. H.; Hulst, R.; Verboom,W.; Reinhoudt,D.N.; Rissanen, K.;Udachin, K. A.; Ripmeester, J. Chem. Eur. J. 1997, 3, 1823-1832.
46. (h) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469-472.
47. (i) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239-241.
48. (j) Vreekamp, R. H.; van Duynhoven, J. P. M.; Hubert, M.; Verboom, W.; Reinhoudt, D. N. Angew. Chem. Int. Ed. 1996, 35, 1215-1218.
49. Wyler, R.; de Mendoza, J.; Rebek, J., Jr. Angew. Chem. Int. Ed. 1993, 32, 1699-1671.
50. (a) Cresswell, A. L.; Piepenbrock, M.-O. M.; Steed, J. W. Chem. Commun. 2010, 46, 2787-2789.
51. (b) Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Eur. J. Org. Chem. 2006, 2810-2816.
52. (c) Corbellini, F.; Knegtel, R. M. A.; Grootenhuis, P. D. J.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Eur. J. 2005, 11, 298-307.
53. (d) Corbellini, F.; Costanzo, L. D.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947.
54. (e) Zadmard, R.; Junkers, M.; Schrader, T.; Grawe, T.; Kraft, A. J. Org. Chem. 2003, 68, 6511-6521.
55. (f) Zadmard, R.; Schrader, T.; Grawe, T.; Kraft, A. Org. Lett. 2002, 4, 1687-1690.
56. (g) Corbellini, F.; Flammengo, R.; Timmerman, P.; Crego-Calama, M.; Versluis, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 6569-6575.
57. (a) Ananchenko, G. S.; Moudrakovski, I. L.; Coleman, A. W.; Ripmeester, J. A. Angew. Chem. Int. Ed. 2008, 47, 5616-5618.
58. (b) Coleman, A. W.; Jebors, S.; Shahgaldian, P.; Ananchenko, G. S.; Ripmeester, J. A. Chem. Commun. 2008, 2291-2303.
59. (c) Ananchenko, G. S.; Udachin, K. A.; Pojarova, M.; Jebors, S.; Coleman, A. W.; Ripmeester, J. A. Chem. Commun. 2007, 707-709.
60. (d) Ananchenko, G. S.; Udachin, K. A.; Dubes, A.; Ripmeester, J. A.; Perrier, T.; Coleman, A. W. Angew. Chem. Int. Ed. 2006, 45, 1585-1588.
61. (e) Ananchenko, G. S.; Udachin, K. A.; Pojarova, M.; Dubes, A.; Ripmeester, J. A.; Jebors, S.; Coleman, A. W. Cryst. Growth Des. 2006, 6, 2141-2148.
62. (f) Ananchenko, G. S.; Udachin, K. A.; Ripmeester, J. A.; Perrier, T.; Coleman, A. W. Chem. Eur. J. 2006, 12, 2441-2447.
63. (a) Jin, Y.; Voss, B. A.; Noble, R. D.; Zhang, W. Angew. Chem. Int. Ed. 2010, 49, 6348-6351.
64. (b) Hasell, T.; Wu, X.; Jones, J. T. A.; Bacsa, J.; Steiner, A.; Mitra, T.; Trewin, A.; Adams, D. J.; Cooper, A. I. Nature Chem. 2010, 2, 750-755.
65. (c) Tozawa, T.; et al. Nature Mater. 2009, 8, 973-978.
66. (d) Tartaggia, S.; Scarso, A.; Padovan, P.; De Lucchi, O.; Fabris, F. Org. Lett. 2009, 11, 3926-3929.
67. (e) Liu, X.; Sun, J.; Warmuth, R. Tetrahedron 2009, 65, 7303-7310.
68. (f) Xu, X.-N.; Wang, L.; Wang, G.-T.; Lin, J.-B.; Li, G.-Y.; Jiang, X.-K.; Li, Z.-T. Chem. Eur. J. 2009, 15, 5763-5774.
69. (g) Steinmetz, V.; Couty, F.; David, O. R. P. Chem. Commun. 2009, 343-345.
70. (h) Skowronek, P.; Gawronski, J. Org. Lett. 2008, 10, 4755-4758.
71. (i) Mastalerz, M. Chem. Commun. 2008, 4756-4758.
72. (j) Kunert, N.; Le-Gresley, A. Tetrahedron Lett. 2008, 49, 1274-1276.
73. (k) Xu, D.; Warmuth, R. J. Am. Chem. Soc. 2008, 130, 7520-7521.
74. (l) Liu, Y.; Liu, X.; Warmuth, R. Chem. Eur. J. 2007, 13, 8953-8959.
75. (m) Liu, X.; Warmuth, R. J. Am. Chem. Soc. 2006, 128, 14120-14127.
76. (n) Liu, X.; Liu, Y.; Li, G.; Warmuth, R. Angew. Chem. Int. Ed. 2006, 45, 901-904.
77. (a) Nishimura, N.; Kobayashi, K. J. Org. Chem. 2010, 75, 6079-6085.
78. (b) Nishimura, N.; Yoza, K.; Kobayashi, K. J. Am. Chem. Soc. 2010, 132, 777-790.
79. (c) Takahagi, H.; Fujibe, S.; Iwasawa, N. Chem. Eur. J. 2009, 15, 13327-13330.
80. (d) Ic-li, B.; Christinat, N.; Tönnemann, J.; Schüttler, C.; Scopelliti, R.; Severin, K. J. Am. Chem. Soc. 2009, 131, 3154-3155.
81. (e) Kataoka, K.; Okuyama, S.; Minami, T.; James, T. D.; Kubo, Y. Chem. Commun. 2009, 1682-1684.
82. (f) Nishimura, N.; Kobayashi, K. Angew. Chem. Int. Ed. 2008, 47, 6255-6258.
83. (g) Christinat, N.; Scopelliti, R.; Severin, K. Angew. Chem. Int. Ed. 2008, 47, 1848-1852.
84. (h) Salazar-Mendoza, D.; Guerrero-Alvarez, J.; Höpfl, H. Chem. Commun. 2008, 6543-6545.
85. (i) Hutin, M.; Bernardinelli, G.; Nitschke, J. R. Chem. Eur. J. 2008, 14, 4585-4593.
86. (j) Kataoka, K.; James, T. D.; Kubo, Y. J. Am. Chem. Soc. 2007, 129, 15126-15127.
87. (k) Barba, V.; Betanzos, I. J. Organomet. Chem. 2007, 692, 4903-4908.
88. Reviews: (a) Severin, K. Dalton Trans. 2009, 5254-5264.
89. (b) Fujita, N.; Shinkai, S.; James, T. D. Chem. Asian J. 2008, 3, 1076-1091.
90. Horng, Y.-C.; Lin, T.-L.; Tu, C.-Y.; Sung, T.-J.; Hsieh, C.-C.; Hu, C.-H.; Lee, H. M.; Kuo, T.-S. Eur. J. Org. Chem. 2009, 1511-1514.
91. (a) Cambell, V. E.; Nitschke, J. R. Synlett 2008, 3077-3090.
92. (b) Meyer, C. D.; Joiner, C. S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 1705-1723.
93. (c) Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112.
94. (d) Fan, J.; Bats, J. W.; Schmittel, M. Inorg. Chem. 2009, 48, 6338-6340.
95. (a) Brumaghim, J. L.; Michels, M.; Raymond, K. N. Eur. J. Org. Chem. 2004, 4552-4559.
96. (b) Brumaghim, J. L.; Michels, M.; Pagliero, D.; Raymond, K. N. Eur. J. Org. Chem. 2004, 5115-5118.
97. (c) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem. Int. Ed. 2000, 39, 4119-4121.
98. (d) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem. Int. Ed. 1998, 37, 1840-1843.
99. (e) Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003-8004.
100. (f) Beissel, T.; Powers, R. E.; Raymond, K. N. Angew. Chem. Int. Ed. 1996, 35, 1084-1086.
101. (a) Argent, S. P.; Riis-Johannessen, T.; Jeffery, J. C.; Harding, L. P.; Ward, M. D. Chem. Commun. 2005, 4647-4649.
102. (b) Paul, R. L.; Argent, S. P.; Jeffery, J. C.; Harding, L. P.; Lynam, J. M.; Ward, M. D. Dalton Trans. 2004, 3453-3458.
103. (a) Riddell, I. A.; Smulders, M. M. J.; Clegg, J. K.; Nitschke, J. R. Chem. Commun. 2011, 47, 457-459.
104. (b) Mal, P.; Nitschke, J. R. Chem. Commun. 2010, 46, 2417-2419.
105. (c) Mal, P.; Breiner, B.; Rissanen, K.; Nitschke, J. R. Science 2009, 324, 1697-1699.
106. Granzhan, A.; Riis-Johannessen, T.; Scopelliti, R.; Severin, K. Angew. Chem. Int. Ed. 2010, 49, 5515-5518.
107. (a) Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101-2108.
108. (b) Le Strat, F.; Harroween, D. C.; Maddaluno, J. J. Org. Chem. 2005, 70, 489-498.
109. (c) Azzouz, R.; Bischoff, L.; Fruit, C.; Marsais, F. Synlett 2006, 1908-1912.
110. (a) Piotrowski, H.; Polborn, K.; Hilt, G.; Severin, K. J. Am. Chem. Soc. 2001, 123, 2699-2700.
111. (b) Piotrowski, H.; Hilt, G.; Schulz, A.; Mayer, P.; Polborn, K.; Severin, K. Chem. Eur. J. 2001, 7, 3196-3208.
112. (a) Gao, J.; Rochat, S.; Qian, X.; Severin, K. Chem. Eur. J. 2010, 16, 513-5017.
113. (b) Rochat, S.; Severin, K. Org. Biomol. Chem. 2009, 7, 1147-1153.
114. (c) Katsuta, S.; Imoto, T.; Kudo, Y.; Takeda, Y. Anal. Sci. 2008, 24, 1215-1217.
115. (d) Katsuta, S.; Iwabe, Y.; Kato, Y.; Kudo, Y.; Takeda, Y. Inorg. Chim. Acta 2008, 361, 103-108.
116. (e) Mimassi, L.; Cordier, C.; Guyard-Duhayon, C.; Mann, B. E.; Amouri, H. Organometallics 2007, 26, 860-864.
117. (f) Grote, Z.; Wizemann, H.-D.; Scopelliti, R.; Severin, K. Z. Anorg. Allg. Chem. 2007, 633, 858-864.
118. (g) Grote, Z.; Scopelliti, R.; Severin, K. J. Am. Chem. Soc. 2004, 126, 16959-16972.
119. (h) Mimassi, L.; Guyard-Duhayon, C.; Rager, M. N.; Amouri, H. Inorg. Chem. 2004, 43, 6644-6649.
120. (i) Grote, Z.; Lehaire, M.-L.; Scopelliti, R.; Severin, K. J. Am. Chem. Soc. 2003, 125, 13638-13639.
121. (j) Lehaire, M.- L.; Schulz, A.; Scopelliti, R.; Severin, K. Inorg. Chem. 2003, 42, 3576-3581.
122. (k) Piotrowski, H.; Severin, K. Proc. Natl. Acad. Sci. U. S.A. 2002, 99, 4997-5000.
123. (a) Olivier, C.; Grote, Z.; Solari, E.; Scopelliti, R.; Severin, K. Chem. Commun. 2007, 4000-4002.
124. (b) Lehaire, M.-L.; Scopelliti, R.; Severin, K. Angew. Chem. Int. Ed. 2002, 41, 1419-1421.
125. (a) Grote, Z.; Scopelliti, R.; Severin, K. Eur. J. Inorg. Chem. 2007, 694-700.
126. (b) Saur, I.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2006, 12, 1058-1066.
127. (c) Grote, Z.; Scopelliti, R.; Severin, K. Angew. Chem. Int. Ed. 2003, 42, 3821-3825.
128. (a) Newman, H. Synthesis 1972, 692-693.
129. (b) Men, Y.-B.; Sun, J.; Huang, Z.-T.; Zheng, Q.-Y. Angew. Chem. Int. Ed. 2009, 48, 2873-2876.
130. (a) Solari, E.; Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2009, 28, 4519-4526.
131. (b) Albrecht, C.; Gauthier, S.; Wolf, J.; Scopelliti, R.; Severin, K. Eur. J. Inorg. Chem. 2009, 1003-1010.
132. (c) Wolf, J.; Thommes, K.; Briel, O.; Scopelliti, R.; Severin, K. Organometallics 2008, 27, 4464-4474.
133. (d) Quebatte, L.; Haas, M.; Solari, E.; Scopelliti, R.; Nguyen, Q. T.; Severin, K. Angew. Chem. Int. Ed. 2005, 44, 1084-1088.
134. Chand, D. K.; Bharadwaj, P. K. Tetrahedron 1997, 53, 10517-10522.
135. Ghosh, P.; Bharadwaj, P. K. Dalton Trans 1997, 2673-2676.
136. The volume of the cavity was estimated by calculating the volume of a polyhedron, which fits inside the cage. For details see ref 21.
137. Wallace, K. J.; Hanes, R.; Anslyn, E.; Morey, J.; Kilway, K. V.; Siegel, J. Synthesis 2005, 2080-2083.
138. Stack, T. D. P.; Hou, Z.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6466-6467.
139. (a) Weigelt, S.; Busse, C.; Bombis, C.; Knudsen, M.; Gothelf, K.; Lægsgaard, E.; Besenbacher, F.; Linderoth, T. Angew. Chem. Int. Ed. 2008, 47, 4406-4410.
140. (b) Nielsen, M.; Thomsen, A. H.; Jensen, T. R.; Jakobsen, H. J.; Skibsted, J.; Gothelf, K. V. Eur. J. Org. Chem. 2005, 342-347.
141. (a) Northrop, B. H.; Zheng, Y.-R.; Chi, K.-W.; Stang, P. J. Acc. Chem. Res. 2009, 42, 1554-1563.
142. (b) Mahata, K.; Saha, M. L.; Schmittel, M. J. Am. Chem. Soc. 2010, 132, 15933-15935.
143. Han, J.-M.; Pan, J.-L.; Lei, T.; Liu, C.; Pei, J. Chem. Eur. J. 2010, 16, 13850-13861.
144. The connection of metallamacrocyclic building blocks via additional coordination bonds has been reported: (a) Clegg, J. K.; Iremonger, S. S.; Hayter, M. J.; Southon, P. D.; Macquart, R. B.; Duriska, M. B.; Jensen, P.; Turner, P.; Jolliffe, K. A.; Kepert, C. J.; Meehan, G. V.; Lindoy, L. F. Angew. Chem. Int. Ed. 2010, 49, 1075-1078.
145. (b) Mirtschin, S.; Slabon-Turski, A.; Scopelliti, R.; Velders, A. H.; Severin, K. J. Am. Chem. Soc. 2010, 132, 14004-14005.
146. (c) Clegg, J. K.; Lindoy, L. F.; McMurtrie, J. C.; Schilter, D. Dalton Trans. 2005, 857-864.
147. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. J. Comput. Chem. 2004, 25, 1605-1612.