Conformational flexibility of 1,4-naphthiporphyrin promotes a palladium-mediated contraction of naphthalene to isoindene

Organometallics

Volumn 30, Issue 16, 2011, Pages 4354-4363

  Szyszko, Bartosz ^a   Latos Graz̀yński, Lechosław ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL CHANGE; CONFORMATIONAL FLEXIBILITY; COORDINATION MODES; DIPROTONATION; FOLDED CONFORMATION; FREE BASE; MACROCYCLES; MACROCYCLIC STRUCTURE; MACROCYCLICS; NAPHTHALENE MOIETIES; NAPHTHALENE RING; NMR STUDIES; PALLADIUM CHLORIDE; TETRAHEDRAL CARBON; TRIPYRRANE;

ACETONITRILE; CHLORINE COMPOUNDS; COORDINATION REACTIONS; PALLADIUM; PALLADIUM COMPOUNDS; X RAY CRYSTALLOGRAPHY;

NAPHTHALENE;

EID: 80051762096     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2004139     Document Type: Article

References (67)

1. Pawlicki, M.; Latos-Graz̀yński, L. Carbaporphyrinoids- Synthesis and Coordination Properties. In Handbook of Porphyrin Science: with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp 104-192.
2. Toganoh, M.; Furuta, H. Synthesis and Metal Coordinationof N-Fused and N-confused Porphyrinoids; In Handbook of Porphyrin Science: with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp 295-367.
3. Srinivasan, A.; Furuta, H. Acc. Chem. Res. 2005, 38, 10-20
4. Chmielewski, P. J.; Latos-Graz̀yński, L. Coord. Chem. Rev. 2005, 249, 2510-2533
5. Chmielewski, P. J.; Latos-Graz̀yński, L.; Głowiak, T. J. Am. Chem. Soc. 1996, 118, 5690-5701
6. Schmidt, I.; Chmielewski, P. J. Chem. Commun. 2002, 92
7. Schmidt, I.; Chmielewski, P. J.; Ciunik, Z. J. Org. Chem. 2002, 67, 8917
8. Stȩpień, M.; Latos-Graz̀yński, L.; Lash, T. D.; Szterenberg, L. Inorg. Chem. 2001, 40, 6892-6900
9. Furuta, H.; Ishizuka, T.; Osuka, A.; Ogawa, T. J. Am. Chem. Soc. 1999, 121, 2945-2946
10. Hung, C.-H.; Chang, F.-C.; Lin, C.-Y.; Rachlewicz, K.; Stȩpień, M.; Latos-Graz̀yński, L.; Lee, G.-H.; Peng, S.-M. Inorg. Chem. 2004, 43, 4118
11. Hung, C.-H.; Chen, W.-C.; Lee, G.-H.; Peng, S.-M. Chem. Commun. 2002, 1516-1517
12. Ishikawa, Y.; Yoshida, I.; Akaiwa, K.; Koguchi, E.; Sasaki, T.; Furuta, H. Chem. Lett. 1997, 453
13. Stȩpień, M.; Latos-Graz̀yński, L. Chem. Eur. J. 2001, 7, 5113-5117
14. Xiao, Z.; Patrick, B. O.; Dolphin, D. Chem. Commun. 2003, 1062
15. Hung, C.-H.; Chen, W.-C.; Lee, G.-H.; Peng, S.-M. Chem. Commun. 2002, 1516-1517
16. Pawlicki, M.; Kańska, I.; Latos-Graz̀yński, L. Inorg. Chem. 2007, 46, 6575-6584
17. Stȩpień, M.; Latos-Graz̀yński, L.; Szterenberg, L. J. Org. Chem. 2007, 72, 2259-2270
18. Hung, C.-H.; Ching, W.-M.; Chang, G.-F.; Chuang, C.-H.; Chu, H.-W.; Lee, W.-Z. Inorg. Chem. 2007, 46, 10941-10943
19. Hayes, M. J.; Spence, J. D.; Lash, T. D. Chem. Commun. 1998, 2409
20. Stȩpień, M.; Latos-Graz̀yński, L. Org. Lett. 2003, 5, 3379-3381
21. Grzegorzek, N.; Pawlicki, M.; Latos-Graz̀yński, L. J. Org. Chem. 2009, 74, 8547-8553
22. Grzegorzek, N.; Pawlicki, M.; Szterenberg, L.; Latos- Graz̀yński, L. J. Am. Chem. Soc. 2009, 131, 7224-7225
23. Szyszko, B.; Latos-Graz̀yński, L.; Szterenberg, L. Angew. Chem., Int. Ed. 2011, 50, 6587-6591
24. Berlin, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1820-1822
25. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 840-842
26. Kaplan, L.; Wendling, L. A.; Wilzbach, K. E. J. Am. Chem. Soc. 1971, 93, 3819-3820
27. Pope, R. M.; VanOrden, S. L.; Cooper, B. T.; Buckner, S. W. Organometallics 1992, 11, 2001-2003
28. Krempner, C.; Reinke, H.; Wustrack, R. Inorg. Chem. Commun. 2006, 10, 239-242
29. Ellis, D.; McKay, D.; Macgregor, S. A.; Rosair, G. M.; Welch, A. J. Angew. Chem., Int. Ed. 2010, 49, 4943-4945
30. Wentrup, C. Top. Curr. Chem. 1976, 62, 173-251
31. Banks, R. E.; Baelow, M. G.; Venayak, N. D. J. Chem. Soc., Chem. Commun. 1980, 151-152
32. Garcia, R.; Riera, J.; Carilla, J.; Julia, L.; Molins, E.; Miravitlles, C. J. Org. Chem. 1992, 5712-5719
33. Silva, L., Jr. Tetrahedron 2002, 58, 9137-9161
34. Silva, L., Jr.; Siqueira, F. A.; Pedrozo, E. C.; Vieira, F. Y. M.; Doriguetto, A. C. Org. Lett. 2007, 9, 1433-1436
35. Bianco, G. G.; Ferraz, H. M. C.; Costa, A. M.; Costa-Lotufo, L.; Pessoa, C.; de Moraes, M. O.; Schrems, M. G.; Pfaltz, A.; Silva, L., Jr. J. Org. Chem. 2009, 74, 2561-2566
36. Scott, L. T.; Agopian, G. K. J. Am. Chem. Soc. 1977, 99, 4506-4507
37. Scott, L. T.; Hasemi, M. M.; Schultz, T. H.; Wallace, M. B. J. Am. Chem. Soc. 1991, 113, 9692-9693
38. Necula, A.; Scott, L. T. J. Anal. Appl. Pyrolysis 2000, 54, 65-87
39. Sattler, A.; Parkin, G. Nature 2009, 463, 523-526
40. Lash, T. D. Eur. J. Org. Chem. 2007, 5461-5481
41. Stȩpień, M.; Latos-Graz̀yński, L. J. Am. Chem. Soc. 2002, 124, 3838-3839
42. Stȩpień, M.; Latos-Graz̀yński, L.; Szterenberg, L.; Panek, J.; Latajka, Z. J. Am. Chem. Soc. 2004, 126, 4566-4580
43. Stȩpień, M.; Szyszko, B.; Latos-Graz̀yński, L. Org. Lett. 2009, 11, 3930-3933
44. Hung, C.-H.; Lin, C.-Y.; Lin, P.-Y.; Chen, Y.-J. Tetrahedron Lett. 2004, 45, 129-132
45. Berlicka, A.; Latos-Graz̀yński, L.; Lis, T. Angew. Chem., Int. Ed. 2005, 44, 5288-5291
46. After submission of this paper the synthesis of 1,4-naphthiporphyrin via an alternative approach, i.e. the direct condensation of 1,4- bis(phenylhydroxymethyl)naphthalene, pyrrole, and arylaldehyde, was reported: Lash, T. D.; Young, A., M.; Rasmussen, M. J.; Ferrence, G., M. J. Org. Chem. 2011, 76, 5636-5651
47. Myśliborski, R.; Latos-Graz̀yński, L. Eur. J. Org. Chem. 2005, 5039-5048
48. Vogel, E.; Röhrig, P.; Sicken, M.; Knipp, B.; Herrmann, A.; Pohl, M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1651-1655
49. Stȩpień, M.; Latos-Graz̀yński, L.; Szterenberg, L. Inorg. Chem. 2004, 43, 6654-6662
50. Stȩpień, M.; Latos-Graz̀yński, L. Aromaticity and tautomerism in porphyrins and porphyrinoids. In Aromaticity in Heterocyclic Compounds; Krygowski, T. M.; Cyrański, M. K., Eds.; Springer: Berlin/Heidelberg, 2009; pp 83-154.
51. Stȩpień, M.; Sprutta, N.; Latos-Graz̀yński, L. Angew. Chem., Int. Ed. 2011, 50, 4288-4340
52. Rachlewicz, K.; Latos-Graz̀yński, L.; Gebauer, A.; Vivian, A.; Sessler, J. L. J. Chem. Soc., Perkin Trans.2 1999, 2189-2195
53. Grootenhuis, P. D. J.; Uiterwijk, J. W. H. M.; Reinhoudt, D. N.; van Staveren, C. J.; Sudhölter, E. J. R.; Bos, M.; van Eerden, J.; Klooster, W. T.; Kruise, L.; Harkema, S. J. Am. Chem. Soc. 1986, 108, 780-788
54. Pacholska-Dudziak, E.; Skonieczny, J.; Pawlicki, M.; Szterenberg, L.; Ciunik, Z.; Latos-Graz̀yński, L. J. Am. Chem. Soc. 2008, 130, 6182-6195
55. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
56. Binotti, B.; Bellachioma, G.; Cardaci, G.; Macchion, A.; Zuccaccia, C.; Foresti, E.; Sabatino, P. Organometallics 2006, 2 (1) 346-354
57. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G. J. Chem. Soc., Dalton Trans. 1989, S1-S83
58. Haneline, M. R.; Tsunoda, M.; Gabbai, F. P. J. Am. Chem. Soc. 2002, 124, 3737-3742
59. Stȩpień, M.; Latos-Graz̀yński, L. Acc. Chem. Res. 2005, 38, 88-98
60. Lash, T. D.; Colby, D. A.; Szczepura, L. F. Inorg. Chem. 2004, 43, 5258-5267
61. Skonieczny, J.; Latos-Graz̀yński, L.; Szterenberg, L. Chem. Eur. J. 2008, 4861-4874
62. Muckey, M. A.; Szczepura, L. F.; Ferrence, G. M.; Lash, T. D. Inorg. Chem. 2002, 41, 4840-4842
63. Lash, T. D.; Hayes, M. J.; Spence, J. D.; Muckey, M. A.; Ferrence, G. M.; Szczepura, L. F. J. Org. Chem. 2002, 67, 4860
64. Zhang, J. D.; Wayland, B. B.; Yun, L.; Li, S.; Fu, X. F. Dalton Trans. 2010, 39, 477-483
65. Colby, D. A.; Lash, T. D. Chem. Eur. J. 2002, 8, 5397-5402
66. Graham, S. R.; Colby, D. A.; Lash, T. D. Angew. Chem., Int. Ed. 2002, 41, 1371-1374
67. Ulman, A.; Manassen, J. J. Chem. Soc., Perkin Trans.1 1979, 1066-1069