General synthesis of meso-amidoporphyrins via palladium-catalyzed amidation

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1837-1840

  Gao, Guang Yao ^a   Chen, Ying ^a   Zhang, X Peter ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMO 10,20 DIPHENYLPORPHYRIN; 5,15 DIBROMO 10,20 DIPHENYLPORPHYRIN; AMIDE; BROMINE; LIGAND; PALLADIUM; PHENYL GROUP; PHOSPHINE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

AMIDATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; PRECURSOR; SYNTHESIS;

AMIDES; BROMINE; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; PORPHYRINS;

EID: 2942556560     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049440b     Document Type: Article

References (40)

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6. For a review on this topic, see: Sharman, W. M.; Van Lier, J. E. J. Porphyrins Phthalocyanines 2000, 4, 441-453.
7. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
8. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
9. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
10. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
11. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
12. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
13. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
14. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
15. For selective examples that applied Suzuki and Stille cross-coupling reactions for porphyrin synthesis, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513. (b) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983. (c) Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676. (d) Liu, C.-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1998, 1805. (e) Shi, X.; Amin, R.; Liebeskind, L. S. J. Org. Chem. 2000, 65, 1650. (f) Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228. (g) Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717. (h) Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066. (i) Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075.
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28. While this manuscript was being prepared, a paper utilizing a meso-brominated Ni(II) porphyrin precursor for the preparation of meso-amino-and meso-amidoporphyrins was reported: Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353.
29. For recent examples of palladium-catalyzed amidation, see: (a) Browning, R. G.; Badarinarayana, V.; Mahmud, H.; Lovely, C. J. Tetrahedron 2004, 60, 359. (b) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207. Yin, J.-J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
30. For recent examples of palladium-catalyzed amidation, see: (a) Browning, R. G.; Badarinarayana, V.; Mahmud, H.; Lovely, C. J. Tetrahedron 2004, 60, 359. (b) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207. Yin, J.-J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
31. For recent examples of palladium-catalyzed amidation, see: (a) Browning, R. G.; Badarinarayana, V.; Mahmud, H.; Lovely, C. J. Tetrahedron 2004, 60, 359. (b) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207. (c) Yin, J.-J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
32. For recent examples of palladium-catalyzed amidation, see: (a) Browning, R. G.; Badarinarayana, V.; Mahmud, H.; Lovely, C. J. Tetrahedron 2004, 60, 359. (b) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207. (c) Yin, J.-J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (d) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
33. For examples of meso-amidoporphyrins, see: (a) Jayaraj, K.; Gold, A.; Ball, L. M.; While, P. S. Inorg. Chem. 2000, 39, 3652. (b) Johnson, C. K.; Dolphin, D. Tetrahedron Lett. 1998, 39, 4753. Poignant, G.; Bourseul, A.; Geze, C.; Le Plouzennec, M.; Le Maux, P.; Bondon, A.; Simonneaux, G.; Moinet, C.; Vonarx, V.; Patrice, T. Tetrahedron Lett. 1996, 37, 7511. Konishi, K.; Mori, Y.; Aida, T.; Inoue, S. Inorg. Chem. 1995, 34, 1292.
34. For examples of meso-amidoporphyrins, see: (a) Jayaraj, K.; Gold, A.; Ball, L. M.; While, P. S. Inorg. Chem. 2000, 39, 3652. (b) Johnson, C. K.; Dolphin, D. Tetrahedron Lett. 1998, 39, 4753. Poignant, G.; Bourseul, A.; Geze, C.; Le Plouzennec, M.; Le Maux, P.; Bondon, A.; Simonneaux, G.; Moinet, C.; Vonarx, V.; Patrice, T. Tetrahedron Lett. 1996, 37, 7511. Konishi, K.; Mori, Y.; Aida, T.; Inoue, S. Inorg. Chem. 1995, 34, 1292.
35. For examples of meso-amidoporphyrins, see: (a) Jayaraj, K.; Gold, A.; Ball, L. M.; While, P. S. Inorg. Chem. 2000, 39, 3652. (b) Johnson, C. K.; Dolphin, D. Tetrahedron Lett. 1998, 39, 4753. (c) Poignant, G.; Bourseul, A.; Geze, C.; Le Plouzennec, M.; Le Maux, P.; Bondon, A.; Simonneaux, G.; Moinet, C.; Vonarx, V.; Patrice, T. Tetrahedron Lett. 1996, 37, 7511. Konishi, K.; Mori, Y.; Aida, T.; Inoue, S. Inorg. Chem. 1995, 34, 1292.
36. For examples of meso-amidoporphyrins, see: (a) Jayaraj, K.; Gold, A.; Ball, L. M.; While, P. S. Inorg. Chem. 2000, 39, 3652. (b) Johnson, C. K.; Dolphin, D. Tetrahedron Lett. 1998, 39, 4753. (c) Poignant, G.; Bourseul, A.; Geze, C.; Le Plouzennec, M.; Le Maux, P.; Bondon, A.; Simonneaux, G.; Moinet, C.; Vonarx, V.; Patrice, T. Tetrahedron Lett. 1996, 37, 7511. (d) Konishi, K.; Mori, Y.; Aida, T.; Inoue, S. Inorg. Chem. 1995, 34, 1292.
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39. Most reported examples that applied metal-mediated cross-coupling reactions for porphyrin synthesis employed zinc porphyrins or other metalloporphyrins as the precursors. See refs 4, 5, 8, and 9.
40. We showed previously that free base porphyrins could also be directly used for palladium-catalyzed amination and etheration reactions. See ref 7.