Cascade fluorofunctionalisation of 2,3-unsubstituted indoles by means of electrophilic fluorination

Chemical Communications

Volumn 49, Issue 90, 2013, Pages 10602-10604

  Nguyen, Tuan Minh ^a   Duong, Hung A ^a   Richard, Jean Alexandre ^a   Johannes, Charles William ^a   Pincheng, Fu ^a   Kwong Jia Ye, Danson ^a   Shuying, Eileen Lau ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLIZATION; FLUORINE; HALOGENATION; INDOLES; OXYGEN; SULFONAMIDES; TEMPERATURE;

FLUORINE DERIVATIVE; FLUOROBENZENESULFONIMIDE; INDOLE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; ELECTROPHILICITY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; PRECURSOR; SYNTHESIS;

EID: 84886889906     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc46564k     Document Type: Article

References (26)

1. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity and Applications, Wiley-VCH, Weinheim, 2004.
2. D. O'Hagan, Chem. Soc. Rev., 2008, 37: 308.
3. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37: 320.
4. H. Liu, Z. Gu, X. Jiang, Adv. Synth. Catal., 2013, 335: 617.
5. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem., Int. Ed., 2013, 52: 8214.
6. T. Besset, C. Schneider, D. Cahard, Angew. Chem., Int. Ed., 2012, 51: 5048.
7. C.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, Y.-C. Gu, Chem. Soc. Rev., 2012, 41: 4536.
8. T. Furuya, A. S. Kamlet, T. Ritter, Nature, 2011, 473: 470.
9. P. S. Fier, J. Luo, J. F. Hartwig, J. Am. Chem. Soc., 2013, 135: 2552.
10. Y. Ye, M. Sanford, J. Am. Chem. Soc., 2013, 135: 4648.
11. A. Casitas, M. Canta, M. Sola, M. Costas, X. Ribas, J. Am. Chem. Soc., 2011, 133: 19386.
12. S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Medebielle, V. Gouverneur, J. Am. Chem. Soc., 2013, 135: 2505.
13. Y. H. Lim, Q. Ong, H. A. Duong, T. M. Nguyen, C. W. Johannes, Org. Lett., 2012, 14: 5676.
14. T. Ishimaru, N. Shibata, T. Horikawa, N. Yashuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem., Int. Ed., 2008, 47: 4157.
15. N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem., Int. Ed., 2005, 44: 4204.
16. N. Shibata, T. Ishimaru, E. Suzuki, K. L. Kirk, J. Org. Chem., 2003, 68: 2494.
17. Y. Takeuchi, T. Tarui, N. Shibata, Org. Lett., 2000, 2: 639.
18. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol., 2010, 14: 347.
19. V. I. Minkin, Chem. Rev., 2004, 104: 2751.
20. F. Mancois, J.-L. Pozzo, J. Pan, F. Adamietz, V. Rodriguez, L. Ducasse, F. Castet, A. Plaquet, B. Champagne, Chem. Eur. J., 2009, 15: 2560.
21. S. C. Wilkinson, R. Salmon, V. Gouverneur, Future Med. Chem., 2009, 1: 847.
22. J. R. Wolstenhulme, J. Rosenqvist, O. Lozano, J. Ilupeju, N. Wurz, K. M. Engle, G. V. Pidgeon, P. R. Moore, G. Sanford, V. Gouverneur, Angew. Chem., Int. Ed., 2013, 52: 9796.
23. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science, 2011, 334: 1681.
24. N. Shibata, T. Tarui, Y. Doi, K. L. Kirk, Angew. Chem., Int. Ed., 2001, 40: 4461.
25. O. Lozano, G. Blessley, T. Martinez del Campo, A. M. Thompson, G. T. Giuffredi, M. Bettani, M. Walker, R. Borman, V. Gouverneur, Angew. Chem., Int. Ed., 2011, 50: 8105.
26. R. Lin, S. Ding, Z. Shi, N. Jiao, Org. Lett., 2011, 13: 4498.