Shape-Persistent Macrocycles Based on Acetylenic Scaffolding

Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis

Volumn , Issue , 2008, Pages 185-231

  Sadowy, Amber L ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Acetylenic scaffolding; Intermolecular reactions; Intramolecular reactions; Modern supramolecular chemistry; Shape persistent Macrocycles (SPM); Supramolecular SPMs; Synthesis

Indexed keywords

EID: 84891299694     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621484.ch6     Document Type: Chapter

References (121)

1. Zhang, W. and Moore, J.S. (2006) Angew. Chem. Int. Ed.., 45, 4416-4439; Angew. Chem. 118, 4524-4548.
2. Zhao, D. and Moore, J.S. (2003) Chem. Commun., 807-818.
3. Young, J.K. and Moore, J.S. (1995) in Modern Acetylene Chemistry (eds. F. Diederich and P.J. Stang), Wiley-VCH, Weinheim, Chapter 12.
4. Höger, S. (2005) Angew. Chem. Int. Ed., 44, 3806-3808; Angew. Chem., 117, 3872-3875.
5. Höger, S. (2005) in Acetylene Chemistry (eds. F. Diederich, P.J. Stang and R.R. Tykwinski ), Wiley-VCH, Weinheim, Chapter 10.
6. Jones, C.S., O'Connor, M.J. and Haley, M.M. (2005) in Acetylene Chemistry (eds. F. Diederich, P.J. Stang and R.R. Tykwinski), Wiley-VCH, Weinheim, Chapter 8.
7. Höger, S. (1999) J. Polym. Sci., Part A: Polym. Chem., 37, 2685-2698.
8. Tahara, K. and Tobe, Y. (2006) Chem. Rev., 106, 5274-5290.
9. Spitler, E.L., Johnson, C.A. and Haley, M.M. (2006) Chem. Rev., 106, 53445386.
10. Nielsen, M.B. and Diederich, F. (2005) Chem. Rev., 105, 1837-1867.
11. Marsden, J.A., Palmer, G.J. and Haley, M.M. (2003) Eur. J. Org. Chem., 23552369.
12. Grave, C. and Schlüter, A.D. (2002) Eur. J. Org. Chem., 3075-3098.
13. Gleiter, R. and Hopf, H. (eds.) (2004) Modern Cyclophane Chemistry, Wiley-VCH, Weinheim.
14. Cheng, X.H., Ju, X.P. and Hoeger, S. (2006) Chin. J. Org. Chem., 26, 733-743.
15. Höger, S. (2004) Chem. Eur.J., 10, 1320-1329.
16. Yamaguchi, Y. and Yoshida, Z. (2003) Chem. Eur. J., 9, 5430-5440.
17. Nielsen, M.B., Schreiber, M., Baek, Y. G., Seiler, P., Lecomte, S., Boudon, C., Tykwinski, R.R., Gisselbrecht, J.-P., Gramlich, V., Skinner, P.J., Bosshard, C., Günter, P., Gross, M. and Diederich, F. (2001) Chem. Eur. J., 7, 3263-3280.
18. Glaser, C. (1869) Ber. Dtsch. Chem. Ges., 2, 422-424.
19. For an excellent review, see: Siemsen, P., Livingston, R.C. and Diederich, F. (2005) Angew. Chem. Int. Ed., 39, 26322657; Angew. Chem., 112, 2740-2767.
20. Hay, A.S. (1962) J. Org. Chem., 27, 3320-3321.
21. Eglinton, G. and Galbraith, A.R. (1959) J. Chem. Soc., 889-896.
22. Eglinton, G. and Galbraith, A.R. (1956) Chem. Ind., 737-738.
23. O'Krongly, D., Denmeade, S.R., Chiang, M.Y. and Breslow, R. (1985) J. Am. Chem. Soc., 107, 5544-5545.
24. Rossi, R., Carpita, A. and Bigelli, C. (1985) Tetrahedron Lett., 26, 523-526.
25. Enozawa, H., Hasegawa, M., Takamatsu, D., Fukui, K. and Iyoda, M. (2006) Org. Lett., 8, 1917-1920.
26. Tobe, Y., Utsumi, N., Nagano, A., Sonoda, M. and Naemura, K. (2001) Tetrahedron, 57, 8075-8083.
27. Ge, P.-H., Fu, W., Herrmann, W.A., Herdtweck, E., Campana, C., Adams, R. D. and Bunz, U.H.F. (2000) Angew. Chem. Int. Ed., 39, 3607-3610; Angew. Chem., 112, 3753-3756.
28. Pschirer, N.G., Fu, W., Adams, R.D. and Bunz, U.H.F. (2000) Chem. Commun., 87-88.
29. Zhang, W. and Moore, J.S. (2004) J. Am. Chem. Soc., 126, 12796.
30. Campbell, I.D., Eglinton, G., Henderson, W. and Raphael, R.A. (1966) J. Chem. Soc. Chem. Commun., 87-89.
31. Huynh, C. and Linstrumelle, G. (1988) Tetrahedron, 44, 6337-6344.
32. Iyoda, M., Vorasingha, A., Kuwatani, Y. and Yoshida, M. (1998) Tetrahedron Lett., 39, 4701-4704.
33. Baxter, P.N.W. (2003) Chem. Eur. J., 9, 2531-2541.
34. Shu, L. and Mayor, M. (2006) Chem. Commun., 4134-4136.
35. For an excellent recent example, see: Hoffmann, M., Wilson, C.J., Odell, B. and Anderson, H.L. (2007) Angew. Chem. Int. Ed., 46, 3122-3125; Angew. Chem., 119, 3183-3186.
36. Laughrey, Z.R. and Gibb, B.C. (2005) Top. Curr. Chem., 249, 67-125.
37. Dietrich-Buchecker, C., Colasson, B.X. and Sauvage, J.-P. (2005) Top. Curr. Chem., 249, 261-283.
38. Godt, A. (2004) Eur. J. Org. Chem., 1639-1654.
39. Anderson, S. and Anderson, H.L. (2000) in Templated Organic Synthesis (eds. F. Diederich and P.J. Stang) Wiley-VCH, Weinheim, Chapter 1.
40. Anderson, S., Anderson, H.L. and Sanders, J.K.M. (1993) Acc. Chem. Res., 26, 469-475.
41. Anderson, H.L. and Sanders, J.K.M. (1990) Angew. Chem. Int. Ed. Engl., 29, 1400-1403; Angew. Chem., 102, 14781480.
42. Anderson, H.L. and Sanders, J.K.M. (1989) J. Chem. Soc. Chem. Commun., 1714-1715.
43. Walter, C.J., Anderson, H.L. and Sanders, J.K.M. (1993) J. Chem. Soc. Chem. Commun., 458-460.
44. Moore, J.S., Weinstein, E.J. and Wu, Z. (1991) Tetrahedron Lett., 32, 2465-2466.
45. Yamaguchi, Y., Kobayashi, S., Miyamura, S., Okamoto, Y., Wakamiya, T., Matsubara, Y. and Yoshida, Z. (2004) Angew. Chem. Int. Ed., 43, 366-369; Angew. Chem., 116, 370-373.
46. Nomoto, A., Sonoda, M., Yamaguchi, Y., Ichikawa, T., Hirose, K. and Tobe, Y. (2006) J. Org. Chem., 71, 401-404.
47. Marsden, J.A., Miller, J.J. and Haley, M. M. (2004) Angew. Chem. Int. Ed., 43,16941697; Angew. Chem., 116, 1726-1729.
48. Marsden, J.A., Miller, J.J., Shirtcliff, L. D. and Haley, M.M. (2005) J. Am. Chem. Soc., 127, 2464-2476.
49. Shortell, D.B., Palmer, L.C. and Tour, J. M. (2001) Tetrahedron, 57, 9055-9065.
50. Elliott, E.L., Ray, C.R., Kraft, S., Atkins, J.R. and Moore, J.S. (2006) J. Org. Chem., 71, 5282-5290.
51. Campbell, K., McDonald, R. and Tykwinski, R.R. (2002) J. Org. Chem., 67, 1133-1140.
52. Campbell, K., Kuehl, C.J., Ferguson, M. J., Stang, P.J. and Tykwinski, R.R. (2002) J. Am. Chem. Soc., 124, 72667267.
53. Campbell, K., Ooms, K.J., Wasylishen, R.E. and Tykwinski, R.R. (2005) Org. Lett., 7, 3397-3400.
54. Sun, S.-S. and Lees, A.J. (2001) Organometallics, 20, 2353-2358.
55. Henze, O., Lentz, D., Schäfer, A., Franke, P. and Schlüter, A.D. (2002) Chem. Eur. J., 8, 357-365.
56. Henze, O., Lentz, D. and Schlüter, A.D. (2000) Chem. Eur. J., 6, 2362-2367.
57. Grave, C., Lentz, D., Schäfer, A., Samori, P., Rabe, J.P., Franke, P. and Schlüter, A.D. (2003) J. Am. Chem. Soc., 125, 6907-6918.
58. Opris, D.M., Franke, P. and Schlüter, A. D. (2005) Eur. J. Org. Chem., 822-837.
59. Schmittel, M., Ammon, H., Kalsani, V., Wiegrefe, A. and Michel, C. (2002) Chem. Commun., 2566-2567.
60. Schmittel, M. and Ammon, H. (1999) Synlett, 750-752.
61. Schmittel, M. and Ganz, A. (1997) Chem. Commun., 999-1000.
62. Kalsani, V., Ammon, H., Jäckel, F., Rabe, J.P. and Schmittel, M. (2004) Chem. Eur. J., 10, 5481-5492.
63. Dietrich-Buchecker, C.O., Hemmert, C., Khémiss, A.-K. and Sauvage, J.-P. (1990) J. Am. Chem. Soc., 112, 80028008.
64. Ünsal, Ö. and Godt, A. (1999) Chem. Eur. J., 5, 1728-1733.
65. Bäuerle, P., Ammann, M., Wilde, M., Götz, G., Mena-Osteritz, E., Rang, A. and Schalley, C.A. (2007) Angew. Chem. Int. Ed., 46, 363-368; Angew. Chem., 119, 367-372.
66. For a review of Pt-acetylide macrocycles, see: Kaiser, A. and Bäuerle, P. Top. Curr. Chem., 249, 127-201.
67. Ammann, M., Rang, A., Schalley, C.A. and Bäuerle, P. (2006) Eur. J. Org. Chem., 1940-1948.
68. Zhu, J., Wang, X.-Z., Chen, Y.-Q., Jiang, X.-K., Chen, X.-Z. and Li, Z.-T. (2004) J. Org. Chem., 69, 6221-6227.
69. Droz, A.S., Neidlein, U., Anderson, S., Seiler, P. and Diederich, F. (2001) Helv. Chim. Acta, 84, 2243-2289.
70. Droz, A.S. and Diederich, F. (2000) J. Chem. Soc. Perkin Trans., 1, 4224-4226.
71. Bähr, A., Droz, A.S., Püntener, M., Neidlein, U., Anderson, S., Seiler, P. and Diederich, F. (1998) Helv. Chim. Acta, 81, 1931-1963.
72. Anderson, S. Neidlein, U. Gramlich, V. and Diederich, F. (1995) Angew. Chem. Int. Ed. Engl., 34, 1596-1600; Angew. Chem., 107, 1722-1725.
73. Kawase, T., Darabi, H.R. and Oda, M. (1996) Angew. Chem. Int. Ed. Engl., 35, 2664-2666; Angew. Chem., 108, 28032805.
74. Kawase, T., Ueda, N., Tanaka, K., Seirai, Y. and Oda, M. (2001) Tetrahedron Lett., 42, 5509-5511.
75. Kawase, T., Tanaka, K., Seirai, Y., Shiono, N. and Oda, M. (2003) Angew. Chem. Int. Ed., 42, 5597-5600; Angew. Chem., 115, 5755-5758.
76. Kawase, T., Tanaka, K., Shiono, N., Seirai, Y. and Oda, M. (2004) Angew. Chem. Int. Ed., 43, 1722-1724; Angew. Chem., 116, 1754-1756.
77. Kawase, T. and Oda, M. (2006) Pure Appl. Chem., 78, 831-839.
78. Baxter, P.N.W. (2001) J. Org. Chem., 66, 4170-4179.
79. Baxter, P.N.W. (2002) Chem. Eur. J., 8, 5250-5264.
80. Baxter, P.N.W. (2004) J. Org. Chem., 69, 1813-1821.
81. Baxter, P.N.W. and Dali-Youcef, R. (2005) J. Org. Chem., 70, 4935-4953.
82. Kobayashi, S., Yamaguchi, Y., Wakamiya, T., Matsubara, Y., Sugimoto, K. and Yoshida, Z. (2003) Tetrahedron Lett., 44, 1469-1472.
83. Heuft, M.A. and Fallis, A.G. (2002) Angew. Chem. Int. Ed., 41, 4520-4523; Angew. Chem., 114, 4702-4705.
84. Ma, C., Lo, A., Abdolmaleki, A. and MacLachlan, M.J. (2004) Org. Lett., 6, 3841-3844.
85. Ma, C.T.L. and MacLachlan, M.J. (2005) Angew. Chem. Int. Ed., 44, 4178-4182; Angew. Chem., 117, 4250-4254.
86. Marsella, M.J., Wang, Z.-Q., Reid, R.J. and Yoon, K. (2001) Org. Lett., 3,885-887.
87. Coates, G.W., Dunn, A.R., Henling, L.M., Dougherty, D.A. and Grubbs, R.H. (1997) Angew. Chem. Int. Ed. Engl., 36, 248-251; Angew. Chem., 109, 290-293.
88. Coates, G.W., Dunn, A.R., Henling, L. M., Ziller, J.W., Lobkovsky, E.B. and Grubbs, R.H. (1998) J. Am. Chem. Soc., 120, 3641-3649.
89. Tobe, Y., Utsumi, N., Kawabata, K., Nagano, A., Adachi, K., Araki, S., Sonoda, M., Hirose, K. and Naemura, K. (2002) J. Am. Chem. Soc., 124, 53505364.
90. Lin, C.-H. and Tour, J. (2002) J. Org. Chem., 67, 7761-7768.
91. Höger, S., Bonrad, K., Mourran, A., Beginn, U. and Möller, M. (2001) J. Am. Chem. Soc., 123, 5651-5659.
92. Nakamura, K., Okubo, H. and Yamaguchi, M. (2001) Org. Lett., 3, 1097-1099.
93. Tobe, Y., Utsumi, N., Nagano, A. and Naemura, K. (1998) Angew. Chem. Int. Ed., 37, 1285-1287; Angew. Chem., 110, 1347-1349.
94. Shetty, A.S., Zhang, J. and Moore, J.S. (1996) J. Am. Chem. Soc., 118, 10191027.
95. Zhang, J. and Moore, J.S. (1992) J. Am. Chem. Soc., 114, 9701-9702.
96. Tobe, Y., Nagano, A., Kawabata, K., Sonoda, M. and Naemura, K. (2000) Org. Lett., 2, 3265-3268.
97. Saiki, Y., Sugiura, H., Nakamura, K., Yamaguchi, M., Hoshi, T. and Anzai, J. (2003) J. Am. Chem. Soc., 125, 92689269.
98. Klyatskaya, S., Dingenouts, N., Rosenauer, C., Müller, B. and Höger, S. (2006) J. Am. Chem. Soc., 128, 31503151.
99. Zhang, W., Brombosz, S.M., Mendoza, J.L. and Moore, J.S. (2005) J. Org. Chem., 70, 10198-10201.
100. Zhang, W. and Moore, J.S. (2005) J. Am. Chem. Soc., 127, 11863-11870.
101. Lahiri, S., Thompson, J.L. and Moore, J. S. (2000) J. Am. Chem. Soc., 122, 1131511319.
102. Balakrishnan, K., Datar, A., Zhang, W., Yang, X., Naddo, T., Huang, J., Zuo, J., Yen, M., Moore, J.S. and Zang, L. (2006) J. Am. Chem. Soc., 128, 65766577.
103. Naddo, T., Che, Y., Zhang, W., Balakrishnan, K., Yang, X., Yen, M., Zhao, J., Moore, J.S. and Zang, L. (2007) J. Am. Chem. Soc., 129, 69786979.
104. Zhao, D. and Moore, J.S. (2003) Macromolecules, 36, 2712-2720.
105. Zhao, D. and Moore, J.S. (2002) J. Org. Chem., 67, 3548-3554.
106. Mindyuk, O.Y., Stetzer, M.R., Heiney, P. A., Nelson, J.C. and Moore, J.S. (1998) Adv. Mater., 10, 1363-1366.
107. Seo, S.H., Jones, T.V., Seyler, H., Peters, J.O., Kim, T.H., Chang, J.Y. and Tew, G. N. (2006) J. Am. Chem. Soc., 128, 92649265.
108. Zhang, J. and Moore, J.S. (1994) J. Am. Chem. Soc., 116, 2655-2656.
109. Höger, S., Enkelmann, V., Bonrad, K. and Tschierske, C. (2000) Angew. Chem. Int. Ed., 39, 2268-2270; Angew. Chem., 112, 2355-2358.
110. Höger, S., Cheng, X.H., Ramminger, A.-D., Enkelmann, V., Rapp, A., Mondeshki, M. and Schnell, I. (2005) Angew. Chem. Int. Ed., 44, 2801-2805; Angew. Chem., 117, 2862-2866.
111. For a more detailed discussion ofthe LC and surface chemistry of SPMs such as 141-142, see: Cheng, X., Ver Heyen, A., Mamdouh, W., Uji-i, H., De Schryver, F., Höger, S. and De Feyter, S. (2007) Langmuir, 23, 1281-1286.
112. De Feyter, S., Gesquiěre, A., Abdel-Mottaleb, M.M., Grim, P.C.M., De Schryver, F.C., Meiners, C., Sieffert, M., Valiyaveettil, S. and Müllen, K. (2000) Acc. Chem. Res., 33, 520-531.
113. Ohkita, M., Ando, K., Suzuki, T. and Tsuji, T. (2000) J. Org. Chem., 65, 43854390.
114. Sonoda, M., Sakai, Y., Yoshimura, T., Tobe, Y. and Kamada, K. (2004) Chem. Lett., 33, 972-973.
115. Furukawa, S., Uji-i, H., Tahara, K., Ichikawa, T., Sonoda, M., De Schryver, F.C., Tobe, Y. and De Feyter, S. (2006) J. Am. Chem. Soc., 128, 3502-3503.
116. Fischer, M., Lieser, G., Rapp, A., Schnell, I., Mamdouh, W., De Feyter, S., De Schryver, F.C. and Höger, S. (2004) J. Am. Chem. Soc., 126, 214-222.
117. Borissov, D., Ziegler, A., Höger, S. and Freyland, W. (2004) Langmuir, 20, 2781-2784.
118. Ziegler, A., Mamdouh, W., Ver Heyen, A., Surin, M., Uji-i, H., Abdel-Mottaleb, M.M.S., De Schryver, F.C., De Feyter, S., Lazzaroni, R. and Höger, S. (2005) Chem. Mater., 17, 5670-5683.
119. Pan, G.-B., Cheng, X.-H., Höger, S. and Freyland, W. (2006) J. Am. Chem. Soc., 128, 4218-4219.
120. Krömer, J., Rios-Carreras, I., Fuhrmann, G., Musch, C., Wunderlin, M., Debaerdemaeker, T., Mena-Osteritz, E. and Bäuerle, P. (2000) Angew. Chem. Int. Ed. 39, 34813486; Angew. Chem., 112, 3623-3628.
121. Mena-Osteritz, E. and Bäuerle, P. (2001) Adv. Mater.,13, 243-246.