Formation of N-alkylpyrroles via intermolecular redox amination

Journal of the American Chemical Society

Volumn 131, Issue 46, 2009, Pages 16626-16627

  Pahadi, Nirmal K ^a   Paley, Miranda ^a   Jana, Ranjan ^a   Waetzig, Shelli R ^a   Tunge, Jon A ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; ALKYLPYRROLES; CHEMICAL EQUATIONS; LACTOLS; REDUCING POWER; REDUCTIVE AMINATION;

ALDEHYDES; ALKYLATION; AMINES; KETONES; REDUCING AGENTS;

AMINATION;

ALDEHYDE; BRONSTED ACID; KETONE; PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; OXIDATION REDUCTION REACTION; REDUCTION; STOICHIOMETRY;

ALDEHYDES; AMINATION; ISOMERISM; KETONES; LACTONES; OXIDATION-REDUCTION; PYRROLES;

EID: 70450169585     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907357g     Document Type: Article

References (23)

1. Recent reactions that proceed via redox isomerization: (a) Verboom, W.; Reinhoudt, D. N.; Visser, R.; Harkema, S. J. Org. Chem. 1984, 49, 269-276.
2. (b) Mátyus, P.; É liás, O.; Tapolcsányi, P.; Polonka-Bálint, A.; Halász- Dajka, B. Synthesis 2006, 16, 2625-2639.
3. (c) McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972-2975.
4. (d) McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131, 402-403.
5. (e) Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 2008, 130, 11970-11978.
6. (f) Han, S. B.; Kim, I. S.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 6916-6917.
7. (a) Mahrwald, R. Curr. Org. Chem. 2003, 7, 1713-1723.
8. (b) Seki, T.; Nakajo, T.; Onaka, M. Chem. Lett. 2008, 35, 824-829.
9. (a) Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009, 74, 419-422.
10. (b) Zhang, C.; De, C. K.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416-417.
11. (c) Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129-132.
12. (a) Schmuck, C.; Rupprecht, D. Synthesis 2007, 3095-3110.
13. (b) Ferreira, V. F.; De Souza, M. C. B. V.; Cunha, A. C.; Leticia, O. R.; Ferreira, M. L. Org. Prep. Proc. Int. 2001, 33, 411-454.
14. (c) Lea, Z.-G.; Chen, Z.-C.; Hu, Y.; Zheng, Q.-G. Synthesis 2004, 1951-1954.
15. (d) Zeng, D. X.; Chen, Y. Synlett 2006, 490-492.
16. (e) Rao, H. S. P.; Jothilingam, S.; Scheeren, H. W. Tetrahedron 2004, 60, 1625-1630.
17. (f) Okada, E.; Masuda, R.; Hojo, M.; Reiko, Y. Heterocycles 1992, 34, 1435-11431
18. (g) Evans, D. A.; Borg, G.; Scheidt, K. A. Angew. Chem., Int. Ed. 2002, 41, 3188-3191.
19. Murahashi, S.-I.; Makabe, Y.; Kunita, K. J. Org. Chem. 1988, 53, 4489-4495.
20. Cook, A. G.; Switek, K. A.; Cutler, K. A.; Witt, A. M. Lett. Org. Chem. 2004, 1, 1-5.
21. A similar reaction has been proposed for the condensation of 3-pyrroline with a p-quinone. Lee, Y.; Ling, K.-Q.; Lu, X.; Silverman, R. B.; Shepard, E. M.; Dooley, D. M.; Sayre, L. M. J. Am. Chem. Soc. 2002, 124, 12135-12143.
22. 3-Pyrroline is commercially available but is expensive (97% $129/g; 65% $52/g) and readily oxidized by air.
23. Li, K.; Tunge, J. A. J. Org. Chem. 2008, 73, 8651-8653.