Facile and efficient synthesis of meso-arylamino- and alkylamino-substituted porphyrins via palladium-catalyzed amination

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4432-4438

  Chen, Ying ^a   Zhang, X Peter ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

AMINES; CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

(5 BROMO 10,20 DIPHENYLPORPHYRINO)ZINC; (5,15 DIBROMO 10,20 DIPHENYLPORPHYRINO)ZINC; ALIPHATIC AMINE; BIS(2 DIPHENYLPHOSPHINOPHENYL) ETHER; METALLOPORPHYRIN; PALLADIUM; PALLADIUM ACETATE; PHOSPHINE DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; HALOGENATION; LIGAND BINDING; METAL BINDING; PRODUCT RECOVERY; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 0038779362     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034063m     Document Type: Article

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40. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
41. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
42. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
43. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
44. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
45. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
46. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
47. For other synthetic methods of meso-arylamino- and alkylamino-substituted porphyrins, see: (a) Screen, T. E. O.; Blake, I. M.; Rees, L. H.; Clegg, W.; Borwick, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans. 1 2002, 320. (b) Jayaraj, K.; Gold, A.; Ball, L. M.; White, P. S. Inorg. Chem. 2000, 39, 3652. (c) Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. Chem. Commun. 1995, 1077. (d) Smith, K. M.; Minnetian, O. M. J. Org. Chem. 1985, 50, 2073. (e) Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953. (f) Connor, W. M.; Straub, D. S. Inorg. Chem. 1976, 15, 2289. (g) Ichimura, K. Chem. Lett. 1976, 6411. (h) Grigg, R. Chem. Commun. 1967, 1238. (i) Johnson, A. W.; Oldfield, D. Tetrahedron Lett. 1964, 5, 1615.
48. 3 was ineffective for the reaction. Only a very small amount of product was observed and most of the starting material remained unchanged by the end of the reaction.