Unified strategy for Iodine(III)-Mediated Halogenation and azidation of 1,3-Dicarbonyl compounds

Organic Letters

Volumn 16, Issue 2, 2014, Pages 600-603

  Galligan, Marc J ^a   Akula, Ramulu ^a   Ibrahim, Hasim ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896782709     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403504z     Document Type: Article

References (46)

1. For a key review on α-azido carbonyl compounds, see: Patonay, T.; Konya, K.; Juhasz-Toth, E. Chem. Soc. Rev. 2011, 40, 2797.
2. For example, see: Shibatomi, K.; Soga, Y.; Narayama, A.; Fujisawa, I.; Iwasa, S. J. Am. Chem. Soc. 2012, 134, 9836.
3. Czekelius, C.; Tzschucke, C. C. Synthesis 2010, 543.
4. Ueda, M.; Kano, T.; Maruoka, K. Org. Biomol. Chem. 2009, 7, 2005.
5. Klimczyk, S.; Huang, X.; Farès, C.; Maulide, N. Org. Biomol. Chem. 2012, 10, 4327.
6. Akula, R.; Galligan, M. J.; Ibrahim, H. Synthesis 2011, 347.
7. Kim, J.-J.; Kweon, D.-H.; Cho, S.-D.; Kim, H.-K.; Lee, S.-G.; Yoon, Y.-J. Synlett 2006, 194.
8. Khan, A. T.; Goswami, P.; Choudhury, L. H. Tetrahedron Lett. 2006, 47, 2751.
9. Brown, M.; Farid, U.; Wirth, T. Synlett 2013, 424.
10. Merritt, E. A.; Olofsson, B. Synthesis 2011, 517.
11. Zhdankin, V. V. ARKIVOC 2009, i, 1.
12. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
13. Liu, W. L.; Chen, C.; Zhang, Q.; Zhu, Z.-B. Beilstein J. Org. Chem. 2012, 8, 344.
14. Akula, R.; Galligan, M. J.; Ibrahim, H. Chem. Commun. 2009, 6991.
15. Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735.
16. For iodine(III)-mediated halogenation of other substrates, see: Nocquet-Thibault, S.; Retailleau, P.; Cariou, K.; Dodd, R. H. Org. Lett. 2013, 15, 1842 and references therein.
17. Kashinath, D.; Budin, G.; Baati, R.; Meunier, S.; Wagner, A. Tetrahedron Lett. 2009, 50, 5379.
18. Benati, L.; Nanni, D.; Spagnolo, P. J. Org. Chem. 1999, 64, 5132.
19. Benati, L.; Calestani, G.; Nanni, D.; Spagnolo, P. J. Org. Chem. 1998, 63, 4679.
20. Moriarty, R. M.; Vaid, R. K.; Ravikumar, V. T.; Vaid, B. K.; Hopkins, T. E. Tetrahedron 1988, 44, 1603.
21. Telvekar, V. N.; Patile, H. V. Synth. Commun. 2010, 41, 131.
22. Fadnavis, N. W.; Vadivel, S. K.; Sharfuddin, M.; Bhalareo, U. T. Tetrahedron: Asymmetry 1997, 8, 4003.
23. Kumar, D.; Sundaree, S.; Rao, V. S. Synth. Commun. 2006, 36, 1893.
24. Prakash, O.; Pannu, K.; Prakash, R.; Batra, A. Molecules 2006, 11, 523.
25. Lee, J. C.; Lee, J. S. Bull. Korean Chem. Soc. 2005, 26, 1493.
26. Lee, J. C.; Kim, S.; Shin, W. C. Synth. Commun. 2000, 30, 4271.
27. Harschneck, T.; Hummel, S.; Kirsch, S. F.; Klahn, P. Chem.-Eur. J. 2012, 18, 1187.
28. Deng, Q. H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356.
29. Vita, M. V.; Waser, J. Org. Lett. 2013, 15, 3246.
30. The method was employed to showcase functional group transfer from a bulky aryl-λ3-iodane: Murray, S. J.; Müller-Bunz, H.; Ibrahim, H. Chem. Commun. 2012, 48, 6268.
31. Salgaonkar, P. D.; Shukla, V. G.; Akamanchi, K. G. Synth. Commun. 2007, 37, 275.
32. Pedersen, C. M.; Marinescu, L. G.; Bols, M. Org. Biomol. Chem. 2005, 3, 816.
33. Tohma, H.; Egi, M.; Ohtsubo, M.; Watanabe, H.; Takizawa, S.; Kita, Y. Chem. Commun. 1998, 173.
34. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406.
35. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 767.
36. Arimoto, M.; Yamaguchi, H.; Fujita, E.; Nagao, Y.; Ochiai, M. Chem. Pharm. Bull. 1989, 37, 3221.
37. Ehrenfreund, J.; Zhiral, E. Tetrahedron 1972, 28, 1697.
38. Moriarty, R. M.; Khosrowshahi, J. S. Tetrahedron Lett. 1986, 27, 2809.
39. Braddock, D. C.; Cansell, G.; Hermitage, S. A. Synlett 2004, 461.
40. Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192.
41. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687.
42. Cech, F.; Zbiral, E. Tetrahedron 1975, 31, 605.
43. Ochiai, M.; Sueda, T.; Miyamoto, K.; Kiprof, P.; Zhdankin, V. V. Angew. Chem., Int. Ed. 2006, 45, 8203.
44. Ochiai, M. Top. Curr. Chem. 2003, 224, 6-68.
45. Yu, J.; Tian, J.; Zhang, C. Adv. Synth. Catal. 2010, 352, 531.
46. Mizukami, F.; Ando, M.; Tanaka, T.; Imamura. J. Bull. Chem. Soc. Jpn. 1978, 51, 335.