Palladium-catalyzed meso-amination and amidation of porphyrins: Marked acceleration with the Ni(II) central metal ion

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7353-7357

  Takanami, Toshikatsu ^a   Hayashi, Mikiko ^a   Hino, Fumio ^a   Suda, Kohji ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Meso amido substituted porphyrin; Meso amino substituted porphyrin; Palladium catalyzed amidation; Palladium catalyzed amination; Porphyrin; 5 bromo 10,20 diphenylporphyrino Ni(II)

Indexed keywords

AMIDE; AMINE; NICKEL; PALLADIUM; PORPHYRIN DERIVATIVE;

AMIDATION; AMINATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0042381716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01837-9     Document Type: Article

References (28)

1. For a review, see: The Porphyrin Hand Book; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000.
2. Two methods are essentially available for the amination of porphyrins. One is a nucleophilic addition of amides to porphyrin cation radicals followed by deacylation: (a) Jayaraji, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652-3664; and references cited therein. The other is a nitration of porphyrins at the meso- or β-carbon followed by reduction: (b) Redmore, N. P.; Rubtsov, I. V.; Therien, M. J. Inorg. Chem. 2002, 41, 566-570; (c) Arnold, D. P.; Bott, R. C.; Eldridge, H.; Elms, F. M.; Smith, G.; Zojaji, M. Aust. J. Chem. 1997, 50, 495-503; and references cited therein.
3. Two methods are essentially available for the amination of porphyrins. One is a nucleophilic addition of amides to porphyrin cation radicals followed by deacylation: (a) Jayaraji, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652-3664; and references cited therein. The other is a nitration of porphyrins at the meso- or β-carbon followed by reduction: (b) Redmore, N. P.; Rubtsov, I. V.; Therien, M. J. Inorg. Chem. 2002, 41, 566-570; (c) Arnold, D. P.; Bott, R. C.; Eldridge, H.; Elms, F. M.; Smith, G.; Zojaji, M. Aust. J. Chem. 1997, 50, 495-503; and references cited therein.
4. Two methods are essentially available for the amination of porphyrins. One is a nucleophilic addition of amides to porphyrin cation radicals followed by deacylation: (a) Jayaraji, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652-3664; and references cited therein. The other is a nitration of porphyrins at the meso- or β-carbon followed by reduction: (b) Redmore, N. P.; Rubtsov, I. V.; Therien, M. J. Inorg. Chem. 2002, 41, 566-570; (c) Arnold, D. P.; Bott, R. C.; Eldridge, H.; Elms, F. M.; Smith, G.; Zojaji, M. Aust. J. Chem. 1997, 50, 495-503; and references cited therein.
5. Recently Osuka et al. have reported the preparation of meso-imido substituted porphyrins by the nucleophilic trapping of porphyrin cation radicals with imide anions: (a) Yoshida, N.; Ishizuka, T.; Yofu, K.; Murakami, M.; Miyasaka, H.; Okada, T.; Nagata, Y.; Itaya, A.; Cho, H. S.; Kim, D.; Osuka, A. Chem. Eur. J. 2003, 9, 2854-2866.
6. Although palladium-catalyzed amination of porphyrins at the β-position has been reported, no yields were described in this paper: Khan M.M., Ali H., van Lier J.E. Tetrahedron Lett. 42:2001;1617-1651.
7. Chen Y., Zhang X.P. J. Org. Chem. 68:2003;4432-4438.
8. Part of this work was presented at the 28th Symposium on Progress in Organic Reactions and Syntheses, Tama, Tokyo, Japan, November, 2002.
9. Zhang et al. made no comment on the amidation of porphyrins, see Ref. 5.
10. Parent 5-bromo-10,20-diphenylporphyrin was prepared according to the literature method, see Ref. 10f.
11. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
12. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
13. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
14. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
15. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
16. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
17. For reviews and recent leading papers on metal-catalyzed amination and amidation of aryl halides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818; (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp. 131-209; (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048; (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706; (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
18. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
19. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
20. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
21. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
22. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
23. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
24. Several reports have appeared on the transition metal-catalyzed carbon-carbon bond formation of porphyrins at the meso- and β-positions: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515; (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993; (c) Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136; (d) Boyle, R. W.; Johnson, C. K.; Dolphine, D. J. Chem. Soc., Chem. Commun. 1995, 527-528; (e) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677; (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232; (g) Vas, B.; Alvarez, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Tetrahedron Lett. 2001, 42, 7409-7412.
25. tBu/18-crown-6/THF brought about dehalogeneation of the substrate porphyrin, only a trace amount of the desired 3a being obtained.
26. 5Ni 617.2089, found: 617.2088.
27. 5NiO 637.1413, found: 637.1414.
28. 3) δ -3.08 (s, 2H), 2.72-2.82 (m, 2H), 3.20 (t, J=8.0 Hz, 2H), 4.69 (t, J=7.0 Hz, 2H), 7.70-7.73 (m, 6H), 8.12-8.18 (m, 4H), 8.91 (d, J=4.8 Hz, 2H), 8.92 (d, J=4.6 Hz, 2H), 9.12 (d, J=4.8 Hz, 2H), 9.25 (d, J=4.6 Hz, 2H), 10.16 (s, 1H).