A facile palladium-mediated contraction of benzene to cyclopentadiene: Transformations of palladium(II) p-benziporphyrin

Angewandte Chemie - International Edition

Volumn 50, Issue 29, 2011, Pages 6587-6591

  Szyszko, Bartosz ^a   Latos Grazyński, Lechosław ^a   Szterenberg, Ludmiła ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

C C activation; carbaporphyrinoids; palladium; porphyrinoids; ring contraction

Indexed keywords

C-C ACTIVATIONS; C-C DOUBLE BONDS; CARBAPORPHYRINOIDS; CARBON OXIDE; CYCLOPENTADIENES; HYDROXIDE IONS; P-PHENYLENE; PORPHYRINOIDS; RING CONTRACTION; SHIFT REACTIONS;

BENZENE; LEAD OXIDE; OLEFINS;

PALLADIUM COMPOUNDS;

EID: 79959993487     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102218     Document Type: Article

References (40)

1. M. Luria, G. Stein, Chem. Commun. 1970, 1650-1651
2. L. Kaplan, L. A. Wendling, K. E. Wilzbach, J. Am. Chem. Soc. 1971, 93, 3819-3820.
3. C. Guyon, P. Boule, J. Lemaire, Tetrahedron Lett. 1982, 23, 1581-1584
4. C. Guyon, P. Boule, J. Lemaire, New J. Chem. 1984, 8, 685-692
5. C. Richard, P. Krajnik, G. Grabner, Phys. Chem. Chem. Phys. 2010, 12, 14322-14329.
6. A. M. Scheer, C. Mukarakate, D. J. Robichaud, G. B. Ellison, M. R. Nimlos, J. Phys. Chem. A 2010, 114, 9043-9056
7. C. A. Taatjes, D. L. Osborn, T. M. Selby, G. Meloni, A. J. Trevitt, E. Epifanovsky, A. I. Krylov, B. Sirjean, E. Dames, H. Wang, J. Phys. Chem. A 2010, 114, 3355-3370
8. L. Khachatryan, J. Adounkpe, B. Dellinger, J. Phys. Chem. A 2008, 112, 481-487
9. S. Thomas, E. B. Ledesma, M. J. Wornat, Fuel 2007, 86, 2581-2595
10. M. Altarawneh, B. Z. Dlugogorski, E. M. Kennedy, J. C. Mackie, J. Phys. Chem. A 2010, 114, 1098-1108.
11. M. Lanfranchi, L. Prati, M. Rossi, A. Tiripicchio, J. Mol. Catal. A 1995, 101, 75-80.
12. H. F. Bettinger, P. R. Schreiner, H. F. Schaefer III, P. von R. Schleyer, J. Am. Chem. Soc. 1998, 120, 5741-5750.
13. J. A. Field, R. Sierra-Alvarez, Biodegradation 2008, 19, 463-480
14. P. C. A. Bruijnincx, G. Van Koten, R. J. M. K. Gebbink, Chem. Soc. Rev. 2008, 37, 2716-2744
15. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Chem. Rev. 2004, 104, 939-986.
16. R. M. Pope, S. L. VanOrden, B. T. Cooper, S. W. Buckner, Organometallics 1992, 11, 2001-2003.
17. C. Krempner, H. Reinke, R. Wustrack, Inorg. Chem. Commun. 2007, 10, 239-242.
18. A. Sattler, G. Parkin, Nature 2010, 463, 523-526.
19. D. Ellis, D. McKay, S. A. Macgregor, G. M. Rosair, A. J. Welch, Angew. Chem. 2010, 122, 5063-5065
20. Angew. Chem. Int. Ed. 2010, 49, 4943-4945.
21. J. D. Harvey, C. J. Ziegler, Coord. Chem. Rev. 2003, 247, 1-19.
22. M. Stpień, L. Latos-Grażyński, Acc. Chem. Res. 2005, 38, 88-98.
23. T. D. Lash, Eur. J. Org. Chem. 2007, 5461-5481.
24. M. Toganoh, H. Furuta, in Handbook of Porphyrin Science: with Applications to Chemistry, Physics, Materials Science Engineering, Biology and Medicine, Vol. 2 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore, 2010, pp. 295-367.
25. M. Pawlicki, L. Latos-Grażyński, in Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science Engineering, Biology and Medicine, Vol. 2 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore 2010, pp. 104-192.
26. CCDC 818561 (2) and 818562 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
27. M. Stpień, L. Latos-Grażyński, J. Am. Chem. Soc. 2002, 124, 3838-3839.
28. M. Stpień, L. Latos-Grażyński, L. Szterenberg, J. Panek, Z. Latajka, J. Am. Chem. Soc. 2004, 126, 4566-4580.
29. E. Pacholska-Dudziak, J. Skonieczny, M. Pawlicki, L. Szterenberg, Z. Ciunik, L. Latos-Grażyński, J. Am. Chem. Soc. 2008, 130, 6182-6195.
30. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
31. B. Binotti, G. Bellachioma, G. Cardaci, A. Macchion, C. Zuccaccia, E. Foresti, P. Sabatino, Organometallics 2006, 21, 346-354.
32. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, J. Chem. Soc. Dalton Trans. 1989, S 1 -S 83.
33. K. Berlin, Angew. Chem. 1996, 108, 1955-1957
34. Angew. Chem. Int. Ed. Engl. 1996, 35, 1820-1822.
35. T. D. Lash, M. J. Hayes, Angew. Chem. 1997, 109, 868-870
36. Angew. Chem. Int. Ed. Engl. 1997, 36, 840-842.
37. J. Skonieczny, L. Latos-Grażyński, L. Szterenberg, Chem. Eur. J. 2008, 14, 4861-4874.
38. J. A. Keith, P. M. Henry, Angew. Chem. 2009, 121, 9200-9212
39. Angew. Chem. Int. Ed. 2009, 48, 9038-9049.
40. J. D. Zhang, B. B. Wayland, L. Yun, S. Li, X. F. Fu, Dalton Trans. 2010, 39, 477-483.