Rhodium catalyzed C2-selective cyanation of indoles and pyrroles

Journal of Organic Chemistry

Volumn 80, Issue 7, 2015, Pages 3695-3700

  Chaitanya, Manthena ^a   Anbarasan, Pazhamalai ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FUNCTIONAL GROUPS;

CYANATION; DIRECTING GROUPS; RHODIUM (III); RHODIUM-CATALYZED;

RHODIUM;

CYANIDE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM; NITRILE;

ARTICLE; CATALYST; CYANATION; FILTRATION; HIGH TEMPERATURE; REACTION OPTIMIZATION; SUBSTITUTION REACTION; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; INDOLES; MOLECULAR STRUCTURE; NITRILES; PYRROLES; RHODIUM;

EID: 84926500845     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00142     Document Type: Article

References (36)

1. Saxton, J. E. Indoles, The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1983; Vol. 25.
2. Jones, R. A. Pyrroles, Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; Vol. 48.
3. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substance: Synthesis, Patents, Applications, 4 th ed.; Georg Thieme: Stuttgart, 2001.
4. Ushijima, S.; Togo, H. Synlett 2010, 1562
5. Nandi, G. C.; Laali, K. K. Tetrahedron Lett. 2013, 54, 2177
6. Khan, T. A.; Peruncheralathan, S.; Ila, H.; Junjappa, H. Synlett 2004, 2019
7. Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049
8. Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513
9. Wen, Q.; Jin, J.; Zhang, L.; Luo, Y.; Lu, P.; Wang, Y. Tetrahedron Lett. 2014, 55, 1271
10. Beck, E. M.; Gaunt, M. J. In C-H Activation; Yu, J.-Q.; Shi, Z., Eds.; Springer: Berlin, 2010; Vol. 292, p 85.
11. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
12. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2009, 110, 624
13. Broggini, G.; Beccalli, E. M.; Fasana, A.; Gazzola, S. Beilstein J. Org. Chem. 2012, 8, 1730
14. Ushijima, S.; Moriyama, K.; Togo, H. Tetrahedron 2012, 68, 4588
15. Smaliy, R. V.; Chaikovskaya, A. A.; Pinchuk, A. M.; Tolmachev, A. A. Synthesis 2002, 2416
16. Tamura, Y.; Kawasaki, T.; Adachi, M.; Tanio, M.; Kita, Y. Tetrahedron Lett. 1977, 18, 4417
17. Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614
18. Liu, B.; Wang, J.; Zhang, B.; Sun, Y.; Wang, L.; Chen, J.; Cheng, J. Chem. Commun. 2014, 50, 2315
19. Ding, S.; Jiao, N. J. Am. Chem. Soc. 2011, 133, 12374
20. Kim, J.; Kim, H.; Chang, S. Org. Lett. 2012, 14, 3924
21. Ren, X.; Chen, J.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 6725
22. Zhang, G.; Lv, G.; Pan, C.; Cheng, J.; Chen, F. Synlett 2011, 2991
23. Reddy, B. V. S.; Begum, Z.; Reddy, Y. J.; Yadav, J. S. Tetrahedron Lett. 2010, 51, 3334
24. Yan, G.; Kuang, C.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 1052
25. Zhang, L.; Wen, Q.; Jin, J.; Wang, C.; Lu, P.; Wang, Y. Tetrahedron 2013, 69, 4236
26. Yuen, O. Y.; Choy, P. Y.; Chow, W. K.; Wong, W. T.; Kwong, F. Y. J. Org. Chem. 2013, 78, 3374
27. Shu, Z.; Ji, W.; Wang, X.; Zhou, Y.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 2186
28. Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5608
29. Liu, W.; Ackermann, L. Chem. Commun. 2014, 50, 1878
30. Hong, X.; Wang, H.; Qian, G.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3228
31. Kou, X.; Zhao, M.; Qiao, X.; Zhu, Y.; Tong, X.; Shen, Z. Chem.-Eur. J. 2013, 19, 16880
32. Pan, C.; Jin, H.; Xu, P.; Liu, X.; Cheng, Y.; Zhu, C. J. Org. Chem. 2013, 78, 9494
33. Saravanan, P.; Anbarasan, P. Org. Lett. 2014, 16, 848
34. Yadagiri, D.; Anbarasan, P. Org. Lett. 2014, 16, 2510
35. Chaitanya, M.; Yadagiri, D.; Anbarasan, P. Org. Lett. 2013, 15, 4960
36. Jones, C. D. J. Org. Chem. 1972, 37, 3624