One-Pot synthesis of indene-expanded porphyrins

Angewandte Chemie - International Edition

Volumn 49, Issue 23, 2010, Pages 3930-3933

  Peterson, Geneva R ^a   Bampos, Nick ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Alkynes; Cyclization; Macrocycles; Porphyrinoids; Zinc

Indexed keywords

CHEMICAL EQUATIONS; EXPANDED PORPHYRINS; IN-SITU; MACROCYCLES; METALATIONS; NOVEL ROUTE; ONE-POT SYNTHESIS; PORPHYRINOIDS;

ACETYLENE; ALDEHYDES; CYCLIZATION; PORPHYRINS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

ZINC;

EID: 77952967228     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906580     Document Type: Article

References (42)

1. R. Paolesse, The Porphyrin Handbook, Vol.2 (Eds.: K.M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, CA, 2000, p. 201;
2. J. L. Sessler, S.J. Weghorn, Expanded, Contracted, and Isomeric Porphyrins, Vol. 15, Elsevier Science, New York, NY, 1997;
3. A. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267.
4. N. Jux, Angew. Chem. 2008, 120, 2577;
5. Angew. Chem. Int. Ed. 2008, 47, 2543;
6. J. Sankar, S. Mori, S. Saito, H. Rath, M. Suzuki, Y. Inokuma, H. Shinokubo, K. S. Kim, Z. S. Yoon, J. Y. Shin, J. M. Lim, Y. Matsuzaki, O. Matsushita, A. Muranaka, N. Kobayashi, D. Kim, A. Osuka, J. Am. Chem. Soc. 2008, 130, 13568;
7. S. Saito, J. Y. Shin, J. M. Lim, K. S. Kim, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 9803;
8. Angew. Chem. Int. Ed. 2008, 47, 9657;
9. M. Stçpień, L. Latos-Grażyński, N. Sprutta, P. Chwalisz, L. Szterenberg, Angew. Chem. 2007, 119, 8015;
10. Angew. Chem. Int. Ed. 2007, 46, 7869.
11. Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693;
12. Angew. Chem. Int. Ed. 2008, 47, 681.
13. J. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292;
14. Angew. Chem. Int. Ed. 2003, 42, 5134.
15. J. M. Lim, Z. S. Yoon, J. Y. Shin, K. S. Kim, M. C. Yoon, D. Kim, Chem. Commun. 2009, 261;
16. R. Misra, T. K. Chandrashekar, Acc. Chem. Res. 2008, 47, 265.
17. L. E. Overman, A. K. Sarkar, Tetrahedron Lett. 1992, 33, 4103.
18. 2 (all data) = 0.1646.
19. 2 (all data) = 0.4353, (isotropic displacement parameters for all but the Cl atoms).
20. H. König, C. Eickmeier, M. Moller, U. Rodewald, B. Franck, Angew. Chem. 1990, 102, 1437;
21. Angew. Chem. Int. Ed. Engl 1990, 29, 1393;
22. S. Beckmann, T. Wessel, B. Franck, W. Honle, H. Borrmann, H. G. Vonschnering, Angew. Chem. 1990, 102, 1439;
23. Angew. Chem. Int. Ed. Engl. 1990, 29, 1395.
24. R. A. Berger, E. LeGoff, Tetrahedron Lett. 1978, 19, 4225.
25. J. L. Sessler, S. J. Weghorn, Y. Hiseada, V. Lynch, Chem. Eur. J. 1995, 1, 56.
26. T. D. Lash, D T. Richter, J. Am. Chem. Soc. 1998, 120, 9965.
27. T.D. Lash, M. J. Hayes, Angew. Chem. 1997, 109, 868;
28. Angew. Chem. Int. Ed Engl. 1997, 36, 840;
29. T. D. Lash, J. L. Romanic, M. J. Hayes, J. D. Spence, Chem. Commun. 1999, 819.
30. T. D. Lash, Eur. J. Org. Chem. 2007, 5461.
31. F. H. Carre, R. J. P. Corriu, G. Bolin, J. J. E. Moreau, C. Vernhet, Organometallics 1993, 12, 2478;
32. J. I. Setsune, K. Watanabe, J. Am. Chem. Soc. 2008, 130, 2404.
33. P. J. Chmielewski, L. Latos-Grazynski, J. Chem. Soc. Perkin Trans. 2 1995, 503;
34. M. J. Webb, Ph.D. thesis, Cambridge University (UK), 2009.
35. 2 (all data) = 0.1301.
36. 2 (all data) = 0.2165.
37. B. Franck, A. Nonn, Angew. Chem. 1995, 107, 1941;
38. Angew. Chem. Int. Ed. Engl. 1995, 34, 1795.
39. J. L. Sessler, E. Tomat, Acc. Chem. Res. 2007, 40, 371;
40. S. Mori, A. Osuka, Inorg. Chem. 2008, 47, 3937;
41. S. Mori, S. Shimizu, J. Y. Shin, A. Osuka, Inorg. Chem. 2007, 46, 4374.
42. 2 (all data) = 0.1026.