One-pot synthesis of meso-alkyl substituted isocorroles: The reaction of a triarylcorrole with Grignard reagent

Journal of Porphyrins and Phthalocyanines

Volumn 14, Issue 8, 2010, Pages 752-757

  Nardis, Sara ^a   Pomarico, Giuseppe ^a   Mandoj, Federica ^a   Fronczek, Frank R ^b   Smith, Kevin M ^b   Paolesse, Roberto ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

corrole; isocorrole; oxidation; synthesis

Indexed keywords

EID: 78149426706     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424610002513     Document Type: Article

References (39)

1. a) The Porphyrin Handbook, Vol. 2, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000.
2. b) Sessler JL and Weghorn SJ. In Expanded, Contracted & Isomeric Porphyrins. Pergamon Press: 2000.
3. a) Vicente MGH. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM and Guilard R. (Eds. Academic Press: San Diego, CA, 2000; pp 149-199.
4. b) Li X, Chmielewski PJ, Xiang J, Xu J, Jiang L, Li Y, Liu H and Zhu D. J. Org. Chem. 2006; 71: 9739-9742.
5. c) Senge MO. Accounts of Chemical Research 2005; 38: 733-743.
6. d) O'Brien AY, McGann JP and Geier GR III. J. Org. Chem. 2007; 72: 4084-4092.
7. e) Abhilash GJ, Bhuyan J, Singh P, Maji S, Pal K and Sarkar S. Inorg. Chem. 2009; 48: 1790-1792.
8. f) Lash TD, El-Beck JA and Colby DA. J. Org. Chem. 2009; 74: 8830-8833.
9. a) Scheer H. Chlorophylls, CRC Press: Boca Raton, FL, 1991.
10. b) Balaban TS. Acc. Chem. Res. 2005; 38: 612-623.
11. c) Senge MO, Wiehe A and Ryppa C. In Advances in Photosynthesis and Respiration, Vol. 25, Grimm B, Porra R, Rudiger W and Scheer H. (Eds.) Springer: Dordrecht, 2006; pp 27-37.
12. Pandey RK and Zheng G. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 157-230.
13. a) Sessler JL and Gale PA. The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, CA, 2000; pp 257-278.
14. b) Sessler JL, Zimmerman RS, Bucher C, Kral V and Andrioletti B. Pure Appl. Chem. 2001; 73: 1041-1057.
15. c) Sessler JL, Gross DE, Chow S, Lynch VM, Schmidtchen FP, Bates GW, Light ME and Gale PA. J. Am. Chem. Soc. 2006; 128: 12281-12288.
16. d) Finnigan EM, Giordani S, Senge OM and McCabe T. J. Phys. Chem. A 2010; 114: 2464-2470.
17. a) Mandoj F, Nardis S, Pomarico G, Stefanelli M, Schiaffino L, Ercolani G, Prodi L, Genovese D, Zaccheroni N, Fronczek FR, Smith KM, Xiao X, Shen J, Kadish KM and Paolesse R. Inorg. Chem. 2009; 48: 10346-10357.
18. b) Stefanelli M, Shen J, Zhu W, Mastroianni M, Mandoj F, Nardis S, Ou Z, Kadish KM, Fronczek FR, Smith KM and Paolesse R. Inorg. Chem. 2009; 48: 6879-6887.
19. c) Mandoj F, Nardis S, Pomarico G and Paolesse R. J. Porphyrins Phthalocyanines 2008; 12: 19-26.
20. d) Stefanelli M, Mastroianni M, Nardis S, Licoccia S, Fronczek FR, Smith KM, Zhu W, Ou Z, Kadish KM and Paolesse R. Inorg. Chem. 2007; 46: 10791-10799.
21. Hohlneicher G, Bremm D, Wytko J, Bley-Escrich J, Gisselbrecht JP, Gross M, Michels M, Lex Johann and Vogel E. Chem. Eur. J. 2003; 9: 5636-5642.
22. Orlewska C, Maes W, Toppet S and Dehaen W. Tetrahedron Lett. 2005; 46: 6067-6070.
23. a) Will S, Rahbar A, Schmickler H, Lex J and Vogel E. Angew. Chem. Int. Ed. Engl. 1990; 29: 1390-1393.
24. b) Vogel E, Binsack B, Hellwig Y, Erben C, Heger A, Lex J and Wu YD. Angew. Chem. Int. Ed. Engl. 1997; 36: 2612-2615.
25. Setsune J, Tsukajima A and Watanabe J. Tetrahedron Lett. 2006; 47: 1817-1820.
26. Flint DL, Fowler RL, LeSaulnier TD, Long AC, O'Brien AY and Geier GR III. J. Org. Chem. 2010; 75: 553-563.
27. Nardis S, Pomarico G, Fronczek FR, Vicente MGH and Paolesse R. Tetrahedron Lett. 2007; 48: 8643-8646.
28. Pomarico G, Xiao X, Nardis S, Paolesse R, Fronczek FR, Smith KM, Fang Y, Ou Z and Kadish KM. Inorg. Chem. 2010; 49: 5766-5774.
29. Setsune J, Tsukajima A and Okazaki N. J. Porphyrins Phthalocyanines 2009; 13: 256-265.
30. Paolesse R, Marini A, Nardis S, Froiio A, Mandoj F, Nurco DJ, Prodi L, Montalti M and Smith KM. J. Porphyrins Phthalocyanines 2003; 7: 25-36.
31. a) Senge MO. Acc. Chem. Res. 2005; 38: 733-743.
32. b) Sergeeva NN, Shaker YM, Finnigan EM, McCabe T and Senge MO. Tetrahedron 2007; 63: 12454-12464.
33. c) Senge MO, Richter J, Bischoff I and Ryan A. Tetrahedron 2010; 66: 3508-3524.
34. Balazs YS, Saltsman I, Mahammed A, Tkachenko E, Golubkov G, Levine J and Gross Z. Magn. Reson. Chem. 2004; 42: 624-635.
35. Du RB, Liu C, Shen DM and Chen QY. Synlett 2009; 16: 2701-2705.
36. Paolesse R, Nardis S, Venanzi M, Mastroianni M, Russo M, Fronczek FR and Vicente MGH. Chem. Eur. J. 2003; 9: 1192-1197.
37. Paolesse R. Synlett 2008: 2215-2230.
38. Nardis S, Mandoj F, Paolesse R, Fronczek FR, Smith KM, Prodi L, Montalti M and Battistini G. Eur. J. Inorg. Chem. 2007; 16: 2345-2352.
39. Gross Z and Mahammed A. J. Porphyrins Phthalocyanines 2002; 6: 553-555.