Guest-selected formation of Pd(II)-linked cages from a prototypical dynamic library [15]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10239-10240

  Hiraoka, Shuichi ^a   Fujita, Makoto ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; GEOMETRY; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033520781     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990733n     Document Type: Letter

References (24)

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2. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
3. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
4. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
5. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
6. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
7. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
8. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
9. Several recent reports deal with the dynamic receptor library: (a) Rowan, S. J.; Sanders, J. K. M. J. Chem, Soc., Perkin Trans. 1 1997, 1407. (b) Brady, P. A. Sanders, J. K. M. J. Chem. Soc., Perkin Trans .1 1997, 3237. (c) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (d) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (e) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (f) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (g) Still, W. C. J. Org. Chem. 1998, 63, 904. (h) Also see: Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
10. Guest-induced assembly of receptors: (a) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (b) Bilyk, A.; Harding, M. M. J. Chem. Soc., Chem. Commun. 1995, 1697.
11. Guest-induced assembly of receptors: (a) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (b) Bilyk, A.; Harding, M. M. J. Chem. Soc., Chem. Commun. 1995, 1697.
12. Guest-templated synthesis of receptors: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
13. Guest-templated synthesis of receptors: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
14. Guest-templated synthesis of receptors: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
15. 4 compounds is involved.
16. Experimental details: see Supporting Information.
17. 3 ring also shows that the rotation of the guest molecule in the cavity is not allowed on the NMR time scale. On the other hand, only one singlet signal is observed for benzene guest, suggesting the rapid spining of the bernzene molecule in the 4·benzene complex on the NMR time scale.
18. The interconversion process is very slow and is negligble within hours if the complex is treated at low temperature and at low concentration. Therefore, pure 4·6 complex can be isolated if it is crystallized and carefully dissolved in water without heating. Upon heating, pure 4·6 complex is again converted into the original 85:15 mixture.
19. 2 with Universal force field: Rappé, A. K.; Cosewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
20. Chiral receptors assembled from achiral building blocks: (a) Rivera, J. M.; Martin, T.; Rebek, J., Jr. Science 1998, 279, 1021. (b) Tokunaga, Y.; Rebek. J., Jr. J. Am. Chem. Soc. 1998, 120, 66.
21. Chiral receptors assembled from achiral building blocks: (a) Rivera, J. M.; Martin, T.; Rebek, J., Jr. Science 1998, 279, 1021. (b) Tokunaga, Y.; Rebek. J., Jr. J. Am. Chem. Soc. 1998, 120, 66.
22. The (P)- and (M)-3 can be defined as follows: (Figure Presented)
23. Guest exchange in encapsulation complexes: (a) Santamaría, J.; Martín, T.; Hilmersson. G.; Craig, S. L.; Rebek. J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8344. (b) Szabo, T.; Hirmersson, G.; Rebek. J., Jr. J. Am. Chem. Soc. 1998, 120, 6193.
24. Guest exchange in encapsulation complexes: (a) Santamaría, J.; Martín, T.; Hilmersson. G.; Craig, S. L.; Rebek. J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8344. (b) Szabo, T.; Hirmersson, G.; Rebek. J., Jr. J. Am. Chem. Soc. 1998, 120, 6193.