The synthesis of indoline and benzofuran scaffolds using a Suzuki-Miyaura coupling/oxidative cyclization strategy

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4426-4429

  Jana, Somnath ^a   Rainier, Jon D ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; INDOLE DERIVATIVE; INDOLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

BENZOFURANS; CATALYSIS; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84883754907     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401974v     Document Type: Article

References (34)

1. Espejo, V. R.; Rainier, J. D. Org. Lett. 2010, 12, 2154
2. Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2006, 45, 4317
3. Nakao, Y.; Yeung, B. K. S.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. J. Am. Chem. Soc. 1995, 117, 8271
4. Yeung, B. K. S.; Nakao, Y.; Kinnel, R. B.; Carney, J. R.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1996, 61, 7168
5. Nakao, Y.; Kuo, J.; Yoshida, W. Y.; Kelly-Borges, M.; Scheuer, P. J. Org. Lett. 2003, 5, 1387
6. Jiao, R.; Xu, S.; Liu, J.; Ge, H.; Ding, H.; Xu, C.; Zhu, H.; Tan, R. Org. Lett. 2006, 8, 5709
7. Konda, Y.; Onda, M.; Hirano, A.; Õmura, S. Chem. Pharm. Bull. 1980, 28, 2987
8. Koizumi, Y.; Arai, M.; Tomoda, H.; Õmura, S. Biochim. Biophys. Acta 2004, 1693, 47
9. Kennedy, A. R.; Taday, M. H.; Rainier, J. D. Org. Lett. 2001, 3, 2407
10. Boyarskikh, V.; Nyong, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2008, 47, 5374
11. Espejo, V. R.; Rainier, J. D. J. Am. Chem. Soc. 2008, 130, 12894
12. Espejo, V. R.; Li, X.-B.; Rainier, J. D. J. Am. Chem. Soc. 2010, 132, 8282
13. Newhouse, T.; Lewis, C. A.; Baran, P. S. J. Am. Chem. Soc. 2009, 131, 6360
14. Snider, B. B.; Wu, X. Org. Lett. 2007, 9, 4913
15. Toumi, M.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 5027
16. Malgesini, B.; Forte, B.; Borghi, D.; Quartieri, F.; Gennari, C.; Papeo, G. Chem.-Eur. J. 2009, 15, 7922
17. Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Synthesis 2009, 2927
18. Newhouse, T.; Lewis, C. A.; Eastman, K. J.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 7119
19. See ref 1a and Espejo, V. R.; Rainier, J. D. Isr. J. Chem. 2011, 51, 473
20. For a recent review, see: de Vries, J. G. Top. Organomet. Chem. 2012, 42, 1
21. For a related NBS induced oxidative cyclization, see: Chang, M.-Y.; Tai, H.-Y.; Chen, Y.-L. Tetrahedron 2011, 67, 7673
22. Liu, G.; Wurst, J. M.; Tan, D. S. Org. Lett. 2009, 11, 3670
23. Robertson, J.; Chovatia, P. T.; Fowler, T. G.; Withey, J. M.; Woollaston, D. J. Org. Biomol. Chem. 2010, 8, 226
24. Potuzak, J. S.; Moilanen, S. B.; Tan, D. S. J. Am. Chem. Soc. 2005, 127, 13796
25. Rodríguez, M.; Boutureira, O.; Matheu, M.; Díaz, Y.; Castillón, S.; Seeberger, P. J. Org. Chem. 2007, 72, 8998
26. Cobo, I.; Matheu, M.; Castillón, S.; Boutureira, O.; Davis, B. Org. Lett. 2012, 14, 1728
27. Fier, P. S.; Luo, J.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2552
28. For seminal work on glycal epoxides and their reactivity, see: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661
29. Rainier, J. D.; Cox, J. M. Org. Lett. 2000, 2, 2707
30. Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997
31. Roberts, S. W.; Rainier, J. D. Org. Lett. 2005, 7, 1141
32. Hubert, J. C.; Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1437
33. Related reactions are known. See: van den Broek, S. A. M. W.; Rensen, P. G. W.; van Delft, F. L.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 5906
34. de Villar, I. S.; Gradillas, A.; Pérez-Castells, J. Eur. J. Org. Chem. 2010, 5850 and the Supporting Information for the synthesis of 26