Multiple deprotonations and deaminations of phenethylamines to synthesize pyrroles

Journal of the American Chemical Society

Volumn 128, Issue 37, 2006, Pages 12046-12047

  Wan, Xiaobing ^a,b   Xing, Dong ^c   Fang, Zhao ^a,b   Li, Bijie ^a,b   Zhao, Fei ^a,b   Zhang, Keya ^a,b   Yang, Liping ^c   Shi, Zhangjie ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBON; COPPER COMPLEX; FERROUS CHLORIDE; HYDROCARBON; HYDROGEN; METAL COMPLEX; NICKEL CHLORIDE; PALLADIUM COMPLEX; PHENETHYLAMINE DERIVATIVE; PLATINUM COMPLEX; PYRROLE DERIVATIVE; SOLVENT; TOLUENE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; DEAMINATION; ELECTRON; HYDROGEN BOND; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 33748790137     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061176p     Document Type: Article

References (41)

1. For reviews on this topic, see: (a) Murai, S. Activation of Unreacîive Bonds and Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, 1999; pp 48-78.
2. (b) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083-4091.
3. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson T. H. Acc. Chem. Res. 1995, 28, 154-162.
4. (d) Sen, A. Acc. Chem. Res. 1998, 31, 550-557.
5. (e) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180-2192.
6. (f) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932 and references therein.
7. (a) Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A.; Zhao, Y.-M.; Xia, W.-J. J. Am. Chem. Soc. 2005, 127, 10836-10837.
8. (b) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935-10941.
9. (c) Chen, H. Y.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995-1997.
10. (d) Lin, M.; Shen, C.; Garcia-Zayas, E. A.; Sen, A. J. Am. Chem. Soc. 2001, 123, 1000-1001.
11. (e) Dangel, B. D.; Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2001, 123, 8149-8150.
12. (f) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857.
13. (g) Giri, R.; Liang, J.; Lei, J.-G.; Li, J.-J.; Wang, D.-H.; Chen, X.; Naggar, I. C.; Guo, C.; Foxman, B. M.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 7420-7424.
14. (h) Jun, C.-H.; Hwang, D.-C.; Na, S.-J. Chem. Commun. 1998, 1405-1406.
15. Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063-3070.
16. (j) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946.
17. (k) Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086-4087.
18. Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1985, 107, 620-631.
19. (m) Shen, C.; Garcia-Zayas, E. A.; Sen, A. J. Am. Chem. Soc. 2000, 122, 4029-4031.
20. (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672-3673.
21. (b) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56-57.
22. (c) Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173-3176.
23. (d) Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. Engl. 2006, 45, 1949-1952.
24. (e) Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242-4243.
25. (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810-11811.
26. (b) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968-6969.
27. (c) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556-6557.
28. (d) Chen, H.; Gan, L.; Shi, Y.; Wei, X. J. Org. Chem. 2001, 66, 6369-6374.
29. (a) Havranek, M.; Singh, A.; Sames, D. J. Am. Chem. Soc. 1999, 121, 8965-8966.
30. (b) Heyduk, A. F.; Driver, T. G.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2004, 126, 15034-15035.
31. (c) Davies, H. M. L.; Jin, Q.; Ren, P.; Kovalenvsky, A. Y. J. Org. Chem. 2002, 67, 4165-4169.
32. (d) Collman, J. P.; Boulatov, R. Inorg. Chem. 2001, 40, 2461-2464.
33. (a) Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002-5011.
34. (b) Kindler, K.; Melamed, G.; Matthies, D. Ann. 1961, 644, 23-30.
35. Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker: New York, 1998.
36. Pyrroles, Part II; Jones, R. A., Ed.; Wiley: New York, 1992.
37. (a) Thompson, R. B. FASEB J. 2001, 15, 1671.
38. (b) Muchowski, J. M. Adv. Med. Chem. 1992, 1, 109.
39. (c) Cozzi, P.; Mongelli, N. Curr. Pharm. Des. 1998, 4, 181.
40. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305-8314.
41. Yang, G.; Wang, A.-L.; Chen, H.-L.; You, Y.-C. Chin. J. Org. Chem. 2005, 25, 641-653 and references therein.