Synthesis and metalation of a chiral, pyridine-strapped, cyclic bis(benzimidazole) ligand

Organic Letters

Volumn 6, Issue 6, 2004, Pages 989-992

  Fekner, Tomasz ^a   Gallucci, Judith ^a   Chan, Michael K ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; COPPER COMPLEX; LIGAND; MACROCYCLIC COMPOUND; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; METALLATION; SYNTHESIS;

EID: 1642569103     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049954a     Document Type: Article

References (29)

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3. (b) Kwok, W.-H.; Zhang, H.; Payra, P.; Duan, M.; Hung, S.-C.; Johnston, D. H.; Gallucci, J.; Skrzypczak-Jankun, E.; Chan, M. K. Inorg. Chem. 2000, 39, 2367-2376.
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5. Fekner, T.; Gallucci, J.; Chan, M. K. J. Am. Chem. Soc. 2004, 126, 223-236.
6. 2 = 0.1580 (all data).
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10. (d) Denat, F.; Lacour, S.; Brandès, S.; Guilard, R. Tetrahedron Lett. 1997, 38, 4417-4420.
11. Although in the literature, the terms "capping" and "strapping" are very often regarded as synonymous, with the former frequently covering all of the possible topologies, we intentionally differentiate between them, in particular when aromatic rings or similar components are used to block one of the macrocyclic faces. When the aromatic ring is, more or less, parallel to the averaged macrocyclic plane, the former serves as a cap. In contrast, when the aromatic ring is approximately perpendicular to the averaged macrocyclic plane, it acts as a strap.
12. 1H NMR) from the purified amine 11, it is postulated that the crude reaction mixture contains a sodium complex of the capped amine 11. The cation may serve as a template on which strapping takes place. However, as a reviewer pointed out, other phenomena (partial protonation, hydration, kinetic alkylation, etc.) might be responsible for the observed spectroscopic discrepancies.
13. 2 = 0.1367 (all data).
14. Jahn, H. A.; Teller, E. Proc. R. Soc. London 1937, 161, 220-235.
15. For reviews on the Jahn-Teller effect in Cu(II) complexes, see: (a) Bersuker, I. B. Chem. Rev. 2001, 101, 1067-1114. (b) The Jahn-Teller Effect. A Bibliographic Review; Bersuker, I. B., Ed.; IFI/Plenum: New York, 1984; pp 1-590. (c) Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118. (d) Bersuker, I. B. Coord. Chem. Rev. 1975, 14, 357-412.
16. For reviews on the Jahn-Teller effect in Cu(II) complexes, see: (a) Bersuker, I. B. Chem. Rev. 2001, 101, 1067-1114. (b) The Jahn-Teller Effect. A Bibliographic Review; Bersuker, I. B., Ed.; IFI/Plenum: New York, 1984; pp 1-590. (c) Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118. (d) Bersuker, I. B. Coord. Chem. Rev. 1975, 14, 357-412.
17. For reviews on the Jahn-Teller effect in Cu(II) complexes, see: (a) Bersuker, I. B. Chem. Rev. 2001, 101, 1067-1114. (b) The Jahn-Teller Effect. A Bibliographic Review; Bersuker, I. B., Ed.; IFI/Plenum: New York, 1984; pp 1-590. (c) Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118. (d) Bersuker, I. B. Coord. Chem. Rev. 1975, 14, 357-412.
18. For reviews on the Jahn-Teller effect in Cu(II) complexes, see: (a) Bersuker, I. B. Chem. Rev. 2001, 101, 1067-1114. (b) The Jahn-Teller Effect. A Bibliographic Review; Bersuker, I. B., Ed.; IFI/Plenum: New York, 1984; pp 1-590. (c) Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118. (d) Bersuker, I. B. Coord. Chem. Rev. 1975, 14, 357-412.
19. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
20. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
21. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
22. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
23. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
24. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
25. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
26. For representative structures of Cu(II) bound to 4N-macrocyclic amine ligands, see: (a) Curtis, N. F.; Gladkikh, O. P. Aust. J. Chem. 2000, 53, 727-741. (b) Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A. G.; Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873-1880. (c) Kim, J. C.; Fettinger, J. C.; Kim, Y. I. Inorg. Chim. Acta 1999, 286, 67-73. (d) Kang, S.-G.; Kim, S.-J.; Jeong, J. H. Polyhedron 1998, 17, 3227-3234. (e) Lancashire, R. J.; Newman, P. D.; Stephens, F. S.; Vagg, R. S.; Williams, P. A. J. Coord. Chem. 1995, 34, 345-350. (f) Bu, X. H.; An, D. L.; Chen, Y. T.; Shionoza, M.; Kimura, E. J. Chem. Soc., Dalton Trans. 1995, 2289-2295. (g) Pattrick, G.; Hancock, R. D. Inorg. Chem. 1991, 30, 1419-1422. (h) Comba, P.; Curtis, N. F.; Lawrance, G. A.; O'Leary, M. A. J. Chem. Soc., Dalton Trans. 1988, 2145-2152.
27. For reviews on nonplanar distortions in other classes of polyazamacrocyclic ligands, see: (a) Senge, M. O. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, Chapter 6, pp 239-347. (b) Shelnutt, J. A.; Song, X.-Z.; Ma, J.-G.; Jia, S.-L.; Jentzen, W.; Medforth, C. J. Chem. Soc. Rev. 1998, 27, 31-41.
28. For reviews on nonplanar distortions in other classes of polyazamacrocyclic ligands, see: (a) Senge, M. O. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, Chapter 6, pp 239-347. (b) Shelnutt, J. A.; Song, X.-Z.; Ma, J.-G.; Jia, S.-L.; Jentzen, W.; Medforth, C. J. Chem. Soc. Rev. 1998, 27, 31-41.
29. 2-catalyzed epoxide-ring opening, see: Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2002, 4, 2817-2819.