Isocyanate as a Versatile Synthon for Modular Synthesis of Functionalized Porphyrins

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2424-2425

  Collman, James P ^a   Wang, Zhong ^a   Straumanis, Andrei ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000110409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980042u     Document Type: Article

References (18)

1. Traylor, T. G. Pure Appl. Chem. 1991, 63, 265.
2. (a) The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978/79; Vol. 1-7.
3. (b) Battersby, A. R. Science 1994, 264, 1551.
4. (c) Collman, J. P. Inorg, Chem. 1997, 36, 5145.
5. Collman, J. P.; Zhang, X.; Herrmann, P. C.; Uffelman, E. S.; Boitrel, B.; Straumanis, A.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 2681. Collman, J. P.; Herrmann, P. C.; Fu, L.; Eberspacher, T. A.; Eubanks, M.; Boitrel, B.; Hayoz, P.; Zhang, X.; Brauman, J. I.; Day, V. W. J. Am. Chem. Soc. 1997, 119, 3481.
6. Collman, J. P.; Zhang, X.; Herrmann, P. C.; Uffelman, E. S.; Boitrel, B.; Straumanis, A.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 2681. Collman, J. P.; Herrmann, P. C.; Fu, L.; Eberspacher, T. A.; Eubanks, M.; Boitrel, B.; Hayoz, P.; Zhang, X.; Brauman, J. I.; Day, V. W. J. Am. Chem. Soc. 1997, 119, 3481.
7. Collman, J. P.; Boitrel, B.; Fu, L.; Galanter, J.; Straumanis, A.; Rapta, M. J. Org. Chem. 1997, 62, 2308.
8. Previously, strong electrophiles such as acid chlorides had exclusively been used for derivatization of TAPP. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. Mansuy, D.; Battioni, P.; Renaud, J.-P.; Guerin, P. J. Chem. Soc., Chem. Commun. 1985, 155. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. Collman, J. P.; Zhang, X.; Lee, V. J. Brauman, J. I. J. Chem. Soc., Chem. Commun. 1992, 1647.
9. Previously, strong electrophiles such as acid chlorides had exclusively been used for derivatization of TAPP. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. Mansuy, D.; Battioni, P.; Renaud, J.-P.; Guerin, P. J. Chem. Soc., Chem. Commun. 1985, 155. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. Collman, J. P.; Zhang, X.; Lee, V. J. Brauman, J. I. J. Chem. Soc., Chem. Commun. 1992, 1647.
10. Previously, strong electrophiles such as acid chlorides had exclusively been used for derivatization of TAPP. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. Mansuy, D.; Battioni, P.; Renaud, J.-P.; Guerin, P. J. Chem. Soc., Chem. Commun. 1985, 155. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. Collman, J. P.; Zhang, X.; Lee, V. J. Brauman, J. I. J. Chem. Soc., Chem. Commun. 1992, 1647.
11. Previously, strong electrophiles such as acid chlorides had exclusively been used for derivatization of TAPP. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. Mansuy, D.; Battioni, P.; Renaud, J.-P.; Guerin, P. J. Chem. Soc., Chem. Commun. 1985, 155. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. Collman, J. P.; Zhang, X.; Lee, V. J. Brauman, J. I. J. Chem. Soc., Chem. Commun. 1992, 1647.
12. Previously, strong electrophiles such as acid chlorides had exclusively been used for derivatization of TAPP. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. Mansuy, D.; Battioni, P.; Renaud, J.-P.; Guerin, P. J. Chem. Soc., Chem. Commun. 1985, 155. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628. Collman, J. P.; Zhang, X.; Lee, V. J. Brauman, J. I. J. Chem. Soc., Chem. Commun. 1992, 1647.
13. Edwards, P. D.; Foster, D. L. D.; Owen, L. N.; Pringle, M. J. J. Chem. Soc., Perkin Trans. 1 1973, 2397. Buntain, I. G.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc., Perkin Trans. 1 1988, 3175.
14. Edwards, P. D.; Foster, D. L. D.; Owen, L. N.; Pringle, M. J. J. Chem. Soc., Perkin Trans. 1 1973, 2397. Buntain, I. G.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc., Perkin Trans. 1 1988, 3175.
15. One previous urea-linked porphyrin system was made via a porphyrin isocyanate; however, the use of phosgene and harsh conditions limited its applications: Collman, J. P.; Brauman, J. I.; Doxsee, K. M.; Halbert, T. R.; Bunnenberg, E.; Linder, R. E.; LaMar, G. N.; Del Gaudio, J.; Lang, G.; Spartalian, K. J. Am. Chem. Soc. 1980, 102, 4182. The several other known urea-functionalized porphyrins were made by combining aminoporphyrins with the few stable aromatic isocyanates: Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
16. One previous urea-linked porphyrin system was made via a porphyrin isocyanate; however, the use of phosgene and harsh conditions limited its applications: Collman, J. P.; Brauman, J. I.; Doxsee, K. M.; Halbert, T. R.; Bunnenberg, E.; Linder, R. E.; LaMar, G. N.; Del Gaudio, J.; Lang, G.; Spartalian, K. J. Am. Chem. Soc. 1980, 102, 4182. The several other known urea-functionalized porphyrins were made by combining aminoporphyrins with the few stable aromatic isocyanates: Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
17. 2 = 1/100) to give 5b (94%).
18. 2. Optimized conditions use alanine sodium salt in the presence of a catalytic amount of tetrabutylammonium bromide to react with TIPP in THF.