Catalytic hydrogenation of meso-octamethylporphyrinogen (Calix[4]pyrrole)

Chemistry - A European Journal

Volumn 16, Issue 14, 2010, Pages 4224-4230

  Journot, Guillaume ^b   Letondor, Christophe ^b   Neier, Reinhard ^b   Stoeckli Evans, Helen ^b   Savoia, Diego ^a   Gualandi, Andrea ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF NEUCHÂTEL   (Switzerland)

Author keywords

Calix 4 pyrrole; Heterogeneous catalysis; Hydrogenation; Nitrogen heterocycles; Porphyrinoids

Indexed keywords

ACIDIC MEDIUMS; ACIDIC SOLVENT; CALIX[4]PYRROLE; CATALYTIC HYDROGENATION; DIASTEREOISOMERS; EXPERIMENTAL CONDITIONS; GC-MS ANALYSIS; HETEROGENEOUS CATALYSIS; HETEROGENEOUS CATALYST; NITROGEN HETEROCYCLES; OCTAMETHYLPORPHYRINOGEN; PORPHYRINOIDS; PYRROLE RING; PYRROLIDINES; REACTION MIXTURE;

CATALYSIS; CATALYSTS; NITROGEN COMPOUNDS;

HYDROGENATION;

CALIXARENE; MESO OCTAMETHYLPORPHYRINOGEN(CALIX(4)PYRROLE); MESO-OCTAMETHYLPORPHYRINOGEN(CALIX(4)PYRROLE); PORPHYRIN; PYRROLE DERIVATIVE; PYRROLIDINE; PYRROLIDINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; SOLUBILITY; STEREOISOMERISM;

CALIXARENES; CATALYSIS; HYDROGENATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PORPHYRINS; PYRROLES; PYRROLIDINES; SOLUBILITY; SOLVENTS; STEREOISOMERISM;

EID: 77950792029     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903464     Document Type: Article

References (87)

1. a) B. Kräutler, Chimia 1987, 41, 277;
2. b) D. Voet, J. G. Voet, Biochemistry, Wiley, New York, 1990, p. 1616;
3. c) H. Scheer, Chlorophylls, CRC Press, Boca Raton, 1991, p. 145;
4. d) B. Kräutler, S. Ostermann, in The Porphyrin Handbook, Vol.11 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2003, p.229;
5. e) B. Kräutler, Biochem. Soc. Trans. 2005, 33, 806-810.
6. a) A. R. Battersby, F. J. Leeper, Top. Curr. Chem. 1998, 195, 143-193;
7. b) H.-J. Kwon, C. S. Wyatt, A. J. Scharon, S. H. Hwang, J. M. Kurth, B. Shen, Science 2002, 297, 1327-1330;
8. c) A. I. Scott, J. Org. Chem. 2003, 68, 2529-2539;
9. d) S. S. Lamb, G. D. Wright, Proc. Natl. Acad. Sci. USA 2005, 102, 519-520.
10. a)P.S. Bryan, J. C. Dabrowiak, Inorg. Chem. 1975, 14, 296-299;
11. b) M. Studer, A. Riesen, T. A. Kaden, Helv. Chim. Acta 1989, 72, 1253-1258;
12. c) E. Kimura, Y. Kodama, M. Shionoya, T. Koike, Inorg. Chim. Acta 1996, 246, 151-158.
13. a) J. T. Groves, T. E. Nemo, J. Am. Chem. Soc. 1983, 105, 5786-5791;
14. b) B. Meunier, E. Guilmet, M. E. De Carvalho, R. Poilblanc, J. Am. Chem. Soc. 1984, 106, 6668-6676;
15. c) W Nam, R. Ho, J. S. Valentine, J. Am. Chem. Soc. 1991, 113, 7052-7054;
16. d) R. Hage, J. E. Iburg, J. Kerschner, J. H. Koek, E. L. M. Lempers, R. J. Martens, U. S. Racherla, S. W. Russell, T. Swarthoff, M. R. P. Vanvliet, J. B. Warnaar, L. Vanderwolf, B. Krijnen, Nature 1994, 369, 637-639;
17. e) D. De Vos, T. Bein, Chem. Commun. 1996, 917-918;
18. f) Z. Guo, P. J. Sadler, Angew. Chem. 1999, 111, 1610-1630;
19. Angew. Chem. Int. Ed. 1999, 38, 1512-1531;
20. g) M.R. Bukowski, K. D. Koehntop, A. Stubna, E. L. Bominaar, J. A. Halfen, E. Muenck, W. Nam, L. Que, Jr., Science 2005, 310, 1000-1002;
21. h) F. Tiago de Oliveira, A. Chanda, D. Banerjee, X. P. Shan, S. Mondai, L. Que, E. L. Bominaar, E. Munck, T. J. Collins, Science 2007, 315, 835-838;
22. i) Y. Kang, H. Chen, Y. J. Jeong, W Lai, E. H. Bae, S. Shaik, W. Nam, Chem. Eur. J. 2009, 15, 10039-10046;
23. j) Y. Gao, T. Åkermark, J. Liu, L. Sun, B. Åkermark, J. Am. Chem. Soc. 2009, 131, 8726-8727.
24. a) F. Tiago de Oliveira, A. Chanda, D. Banerjee, X. Shan, S. Mondal, L. Que, Jr., E. L. Bominaar, E. Muenck, T. J. Collins, Science 2007, 315, 835-838;
25. b) A. J. McGown, W D. Kerber, H. Fujii, D. P. Goldberg, J. Am. Chem. Soc. 2009, 131, 8040-8048.
26. M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194-7195.
27. a) A. L. Gavrilova, B. Bosnich, Chem. Rev. 2004, 104, 349-383;
28. b) K. Nehru, S. J. Kim, I. Y. Kim, M. S. Seo, Y. Kim, S.-J. Kim, J. Kim, W. Nam, Chem. Commun. 2007, 4623-4625;
29. c) J. England, M. Martinho, E. R. Farquhar, J. R. Frisch, E. L. Bominaar, E. Munck, L. Que, Jr., Angew. Chem. 2009, 121, 3676-3680;
30. Angew. Chem. Int. Ed. 2009, 48, 3622-3626.
31. J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435;
32. Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
33. A. Baeyer, Ber. Dtsch. Chem. Ges. 1886, 19, 2184.
34. a) V. V. Chelintzev, B. V. Tronov, S. G. Karmanov, J. Russ. Chem. Soc. 1916, 48, 1210-1221;
35. b) P. Rothemund, C. L. Gage, J. Am. Chem. Soc. 1955, 77, 3340-3342.
36. P. A. Gale, J. L. Sessler, V. Krai, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140-5141.
37. J. L. Sessler, P. A. Gale, in The Porphyrin Handbook, Vol.6 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, p. 257.
38. a) J. Jubb, D. Jacoby, C Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 1306-1308;
39. b) C. Floriani, Chem. Commun. 1996, 1257-1263;
40. c) L. Bonomo, E. Solari, R. Scopelliti, C. Floriani, Chem. Eur. J. 2001, 7, 1322-1332.
41. a) B. Sakurai, Bull. Chem. Soc. Jpn. 1936, 11, 374-376;
42. b) T. J. Donohoe, P. M. Guyo, J. Org. Chem. 1996, 61, 7664-7665;
43. c) T. J. Donohoe, P. M. Guyo, R. R. Harji, M. Helliwell, Tetrahedron Lett. 1998, 39, 3075-3078;
44. d) T. J. Donohoe, P. M. Guyo, M. Helliwell, Tetrahedron Lett. 1999, 40, 435-438;
45. e) K. Hoshino, N. Ozawa, H. Kokado, H. Seki, T. Tokunaga, T Ishikawa, J. Org. Chem. 1999, 64, 4572-4573;
46. f) A. Schafer, B. Schafer, Tetrahedron 1999, 55, 12309-12312;
47. g) T J. Donohoe, H. O. Sintim, Org. Lett. 2004, 6, 2003-2006;
48. h) T. J. Donohoe, H. O. Sintim, L. Sisangia, K. W Ace, P. M. Guyo, A. Cowley, J. D. Harling, Chem. Eur. J. 2005, 11, 4227-4238;
49. i) T. J. Donohoe, R. E. Thomas, Nat. Protoc. 2007, 2, 1888-1895.
50. a) G. Ciamician, M. Dennstedt, Gazz. Chim. Ital. 1883, 13, 395-403;
51. b) G. Ciamician, P. Magnaghi, Gazz. Chim. Ital. 1885, 15, 481-508;
52. c) G. Ciamician, Ber. Dtsch. Chem Ges. 1901, 34, 3952-3955.
53. L. Knorr, P. Rabe, Ber. Dtsch. Chem. Ges. 1901, 34, 3491-3502.
54. a) G. G. Evans, J. Am. Chem. Soc. 1951, 73, 5230-5234;
55. b) D. M. Lemal, S. D. McGregor, J. Am. Chem. Soc. 1966, 88, 1335-1336;
56. c) C. B. Hudson, A. V. Robertson, Tetrahedron Lett. 1967, 8, 4015-4017;
57. d) D. P. Schumacher, S. S. Hall, J. Am Chem. Soc. 1982, 104, 6076-6080;
58. e) B. S. Gourlay, J. H. Ryan, J. A. Smith, Beilstein J. Org. Chem. 2008, 4.
59. a) P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, p. 221;
60. b) G. V. Smith, F. Notheisz, Heterogeneous Catalysis in Organic Chemistry, Academic Press, New York, 1999, p. 346;
61. c) R. A. Sheldon, H. van Bekkum, Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2001, p. 670;
62. d) S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley Interscience, New York, 2001, p. 720.
63. a) L. H. Andrews, S. M. McElvain, J. Am. Chem. Soc. 1929, 51, 887-892;
64. b) A. H. Corwin, Heterocycl. Compds. 1950, 1, 339;
65. c) H. A. Bates, H. Rapoport, J. Am. Chem. Soc. 1979, 101, 1259-1265;
66. d) T. J. Bond, R. Jenkins, A. C. Ridley, P. C. Taylor, J. Chem. Soc. Perkin Trans. 1 1993, 2241-2242;
67. e) C. W. Jefford, K. Sienkiewicz, S. R. Thornton, Tetrahedron Lett. 1994, 35, 4759-4762;
68. f) C. W. Jefford, S. R. Thornton, K. Sienkiewicz, Tetrahedron Lett. 1994, 35, 3905-3908;
69. g) C. W. Jefford, K. Sienkiewicz, S. R. Thornton, Helv. Chim. Acta 1995, 78, 1511-1524;
70. h) T. L. Gilchrist, A. Lemos, C. J. Ottaway, J. Chem. Soc. Perkin Trans. 1 1997, 3005-3012;
71. i) C. W. Jefford, Curr. Org. Chem. 2000, 4, 205-230;
72. j) S. E. Denmark, H. Matsuhashi, J. Org. Chem. 2002, 67, 3479-3486;
73. k) R. I. J. Amos, B. S. Gourlay, P. P. Molesworth, J. A. Smith, O. R. Sprod, Tetrahedron 2005, 61, 8226-8230;
74. l) R. Chenevert, F. Jacques, P. Giguere, M. Dasser, Tetrahedron: Asymmetry 2008, 19, 1333-1338;
75. m) T. Maegawa, A. Akashi, K. Yaguchi, Y. Iwasaki, M. Shigetsura, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2009, 15, 6953-6963.
76. a) W. W. Turner, J. Heterocycl. Chem. 1986, 23, 327-328;
77. b) M. Tokuda, Y. Yamada, T. Takagi, H. Suginome, A. Furusaki, Tetrahedron 1967, 43, 281-296.
78. V. Blangy, C. Heiss, V. Khlebnikov, C. Letondor, H. Stoeckli-Evans, R. Neier, Angew. Chem. 2009, 121, 1716-1719;
79. Angew. Chem. Int. Ed. 2009, 48, 1688-1691.
80. See the Supporting Information.
81. a) D. Savoia, C. Trombini, A. Umani-Ronchi, Pure Appl. Chem. 1985, 57, 1887-1896;
82. b) R. Csuk, B. Gläunzer, A. Fürstner, Organomet. Chem. 1988, 17, 85-137.
83. a) V. G. Albano, A. Gualandi, M. Monari, D. Savoia, J. Org. Chem. 2008, 73, 8376-8381;
84. b) G. Falini, A. Gualandi, D. Savoia, Synthesis 2009, 2440-2446.
85. D. Savoia, C. Trombini, A. Umani-Ronchi, G. Verardo, J. Chem. Soc. Chem. Commun. 1981, 540-541.
86. It has been reported that 1 has higher solubility in methanol as compared to ethanol, N'.N-dimethylformamide, and acetonitrile: A. F. Danil de Namor, M. Shehab, J. Phys. Chem. B 2003, 107, 6462-6468.
87. R. Kuwano, M. Kashiwabara, M. Ohsumi, H. Kusano, J. Am. Chem. Soc. 2007, 129, 808-809.