Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysts

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2622-2625

  Inamoto, Kiyofumi ^a   Asano, Narumi ^a   Nakamura, Yuka ^a   Yonemoto, Misato ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; CARBON DIOXIDE; CARBOXYLIC ACID; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ANILINE COMPOUNDS; CARBON DIOXIDE; CARBOXYLIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE;

EID: 84862106886     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300958c     Document Type: Article

References (38)

1. Louie, J. Curr. Org. Chem. 2005, 9, 605
2. Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365
3. Darensboug, D. J. Chem. Rev. 2007, 107, 2388
4. Correa, A.; Martín, R. Angew. Chem., Int. Ed. 2009, 48, 6201
5. Aresta, M.; Dibenedetto, A. Dalton Trans. 2010, 39, 3347
6. Riduan, S. N.; Zhang, Y. Dalton Trans. 2010, 39, 3347
7. Ackermann, L. Angew. Chem., Int. Ed. 2011, 50, 3842
8. Zhang, Y.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210w
9. Boogaerts, I. I. F.; Nolan, S. P. Chem. Commun. 2011, 47, 3021
10. Takimoto, M.; Nakamura, Y.; Kimura, K.; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956
11. Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2006, 128, 8706
12. Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2681
13. Takaya, J.; Tadami, S.; Ukai, K.; Iwasawa, N. Org. Lett. 2008, 10, 2697
14. Ohishi, T.; Nishimura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792
15. Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 7826
16. Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254
17. Correa, A.; Martín, R. J. Am. Chem. Soc. 2009, 131, 15974
18. Dang, L.; Lin, Z. Organometallics 2010, 29, 917
19. Boogaerts, I. I. F.; Nolan, S. P. J. Am. Chem. Soc. 2010, 132, 8858
20. Zhang, L.; Cheng, J.; Ohishi, T.; Hou, Z. Angew. Chem., Int. Ed. 2010, 49, 8670
21. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem., Int. Ed. 2010, 49, 8674
22. Mizuno, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 1251
23. Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115
24. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285
25. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
26. Vicente, R. Org. Biomol. Chem. 2011, 9, 6469
27. Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799
28. Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803
29. Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355
30. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406
31. Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126
32. Boyer, A.; Isono, N.; Lackner, S.; Leutens, M. Tetrahedron 2010, 66, 6468
33. Swamy, N. K.; Yazici, A.; Pyne, S. G. J. Org. Chem. 2010, 75, 3412
34. Huang, J.; Macdonald, S. J. F.; Harrity, J. P. A. Chem. Commun. 2010, 46, 8770
35. Han, X.; Lu, X. Org. Lett. 2010, 12, 3336
36. 2 has recently been reported; see: Vechorkin, O.; Hirt, N.; Hu, X. Org. Lett. 2010, 12, 3567
37. 2, see: Kobayashi, K.; Kondo, Y. Org. Lett. 2009, 11, 2035
38. Inamoto, K.; Asano, N.; Kobayashi, K.; Yonemoto, M.; Kondo, Y. Org. Biomol. Chem. 2012, 10, 1514