Regioselective Csp2-H dual functionalization of indoles using hypervalent iodine(III): Bromo-amination via 1,3-migration of imides on indolyl(phenyl)iodonium imides

Chemical Communications

Volumn 51, Issue 12, 2015, Pages 2273-2276

  Moriyama, Katsuhiko ^a   Ishida, Kazuma ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; IMIDE; INDOLE DERIVATIVE; INDOLYL(PHENYL)IODONIUM IMIDE; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG; CARBON; HYDROGEN; IODINE;

AMINATION; AROMATIZATION; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CRYSTAL STRUCTURE; ELECTROPHILICITY; ISOMER; MICHAEL ADDITION; NUCLEOPHILICITY; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS;

AMINATION; CARBON; HYDROGEN; IMIDES; INDOLES; IODINE; QUANTUM THEORY; STEREOISOMERISM;

EID: 84921866929     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc09077b     Document Type: Article

References (43)

1. (a) E. C. Taylor and R. A. Jones, Pyrroles, Wiley, New York, 1990;
2. (b) J. E. Saxton, The Chemistry of Heterocyclic Compounds, Wiley Interscience, New York, 1994, vol. 25;
3. (c) R. J. Sundberg, Indoles, Academic, New York, 1996;
4. (d) S.-W. Yang, M. Abdel-Kader, S. Malone, M. C. M. Werkhoven, J. H. Wisse, I. Bursuker, K. Neddermann, C. Fairchild, C. Raventos-Suarez, A. T. Menendez, K. Lane and D. G. I. Kingston, J. Nat. Prod., 1999, 62, 976;
5. (e) D. Crich and A. Banerjee, Acc. Chem. Res., 2007, 40, 151.
6. (a) M. M. Cooper, J. M. Lovell and J. A. Joule, Tetrahedron Lett., 1996, 37, 4283;
7. (b) E. T. Pelkey and G. W. Gribble, Synthesis, 1999, 1117;
8. (c) J. Jiang and G. W. Gribble, Tetrahedron Lett., 2002, 43, 4115;
9. (d) F. Portela-Cubillo, B. A. Surgenor, R. A. Aitken and J. C. Walton, J. Org. Chem., 2008, 73, 8124;
10. (e) J. E. Mangette, X. Chen, R. Krishnamoorthy, A. S. Vellekoop, A. J. Csakai, F. Camara, W. D. Paquette, H.-J. Wang, H. Takahashi, R. Fleck and G. P. Roth, Tetrahedron Lett., 2011, 52, 1292;
11. (f) M. Poirier, S. Goudreau, J. Poulin, J. Savoie and P. L. Beaulieu, Org. Lett., 2010, 12, 2334;
12. (g) R. Ghorbani-Vaghei and S. M. Malaekehpoor, Tetrahedron Lett., 2012, 53, 4751;
13. (h) N. Pidlypnyi, F. Uhrner, M. Nieger, M. H. H. Drafz, E. G. Hübner, J. C. Namyslo and A. Schmidt, Eur. J. Org. Chem., 2013, 7739;
14. (i) S. J. Markey, W. Lewis and C. J. Moody, Org. Lett., 2013, 15, 6306.
15. (a) B. Witulski, C. Alayrac and L. Tevzadze-Saeftel, Angew. Chem., Int. Ed., 2003, 42, 4257;
16. (b) A. Cost, M. Toumi, K. Wright, V. Razafimahaléo, F. Couty, J. Marrot and G. Evano, Org. Lett., 2008, 10, 3841;
17. (c) Q. Shuai, G. Deng, Z. Chua, D. S. Bohle and C.-J. Li, Adv. Synth. Catal., 2010, 352, 632;
18. (d) X.-Y. Liu, P. Gao, Y.-W. Shen and Y.-M. Liang, Org. Lett., 2011, 13, 4196;
19. (e) A. S. Kumar, P. V. A. Rao and R. Nagarajan, Org. Biomol. Chem., 2012, 10, 5084;
20. (f) S. Shi, B. Zhou, Y. Yang and Y. Li, Org. Biomol. Chem., 2012, 10, 8953;
21. (g) D. Lubriks, I. Sokolovs and E. Suna, J. Am. Chem. Soc., 2012, 134, 15436;
22. (h) I. Sokolovs, D. Lubriks and E. Suna, J. Am. Chem. Soc., 2014, 136, 6920.
23. (a) X.-Y. Liu, P. Gao, Y.-W. Shen and Y.-M. Liang, Org. Lett., 2011, 13, 4196;
24. (b) Y.-X. Li, K.-G. Ji, H.-X. Wang, S. Ali and Y.-M. Liang, J. Org. Chem., 2011, 76, 744;
25. (c) Y.-X. Li, H.-X. Wang, S. Ali, X.-F. Xia and Y.-M. Liang, Chem. Commun., 2012, 48, 2343;
26. (d) W.-B. Wu and J.-M. Huang, Org. Lett., 2012, 14, 5832;
27. (e) S. Ali, Y.-X. Li, S. Anwar, F. Yang, Z.-S. Chen and Y.-M. Liang, J. Org. Chem., 2012, 77, 424;
28. (f) H.-H. Liu, Y. Wang, G. Deng and L. Yang, Adv. Synth. Catal., 2013, 355, 3369;
29. (g) B. Prasad, B. Y. Sreenivas, D. Rambabu, G. R. Krishna, C. M. Reddy, K. L. Kumar and M. Pal, Chem. Commun., 2013, 49, 3970.
30. A. John and K. M. Nicholas, Organometallics, 2012, 31, 7914.
31. X.-Y. Liu, P. Gao, Y.-W. Shen and Y.-M. Liang, Org. Lett., 2011, 13, 4196.
32. (a) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123;
33. (b) V. V. Zhdankin and P. J. Stang, Chem. Rev., 2008, 108, 5299.
34. (a) H. J. Kim, J. Kim, S. H. Cho and S. Chang, J. Am. Chem. Soc., 2011, 133, 16382;
35. (b) A. A. Kantak, S. Potavathri, R. A. Barham, K. M. Romano and B. Deboef, J. Am. Chem. Soc., 2011, 133, 19960;
36. (c) K. Kiyokawa, S. Yahata, T. Kojima and S. Minakata, Org. Lett., 2014, 16, 4646.
37. (a) C. Röben, J. A. Souto, Y. González, A. Lishchynskyi and K. Muñiz, Angew. Chem., Int. Ed., 2011, 50, 9478;
38. (b) J. A. Souto, Y. González, A. Iglesias, D. Zian, A. Lishchynskyi and K. Muñiz, Chem. - Asian J., 2012, 7, 1103;
39. (c) J. A. Souto, D. Zian and K. Muñiz, J. Am. Chem. Soc., 2012, 134, 7242;
40. (d) J. A. Souto, C. Martìnez, I. Velilla and K. Muñiz, Angew. Chem., Int. Ed., 2013, 52, 1324.
41. J. A. Souto, P. Brcker, À. Iglesias and K. Muñiz, J. Am. Chem. Soc., 2012, 134, 15505.
42. K. Moriyama, K. Ishida and H. Togo, Org. Lett., 2012, 14, 946.
43. Treatment of 2a with t-BuLi and PhCHO in THF at -96°C did not produce the desired product 6a but instead 5a in 45% yield.