Iodine(III)-mediated ethoxychlorination of enamides with iron(III) chloride

Tetrahedron

Volumn 70, Issue 38, 2014, Pages 6769-6775

  Nocquet Thibault, Sophie ^a   Minard, Corinne ^a   Retailleau, Pascal ^a   Cariou, Kevin ^a   Dodd, Robert H ^a  

^a CNRS   (France)

Author keywords

Hypervalent iodine Umpolung Chlorination Enamides

Indexed keywords

AMIDE; BENZENE; ENAMIDE; FERRIC ION; FERRIC ION CHLORIDE; FREE RADICAL; IODINE DERIVATIVE; IODINE III; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHLORINATION; DIASTEREOISOMER; DRUG MIXTURE; ELECTROPHILICITY; ETHOXYCHLORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MELTING POINT; REACTION TIME; SOLUBILITY; TEMPERATURE; X RAY ANALYSIS;

EID: 84906965284     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.07.066     Document Type: Article

References (52)

1. M. Brown, U. Farid, and T. Wirth Synlett 2013 424
2. V.V. Zhdankin, and P.J. Stang Chem. Rev. 108 2008 5299
3. T. Wirth Angew. Chem., Int. Ed. 44 2005 3656
4. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523
5. A. Varvoglis Tetrahedron 53 1997 1179
6. V.V. Zhdankin, and P.J. Stang Chem. Rev. 96 1996 1123
7. E.A. Merritt, and B. Olofsson Synthesis 2011 517 for recent examples, see
8. M.J. Galligan, R. Akula, and H. Ibrahim Org. Lett. 16 2014 600
9. W.L. Liu, C. Chen, Q. Zhang, and Z.-B. Zhu Beilstein J. Org. Chem. 8 2012 344
10. R. Akula, M. Galligan, and H. Ibrahim Chem. Commun. 2009 6991
11. D. Tu, L. Ma, X. Tong, X. Deng, and C. Xia Org. Lett. 14 2012 4830
12. H. Hamamoto, S. Hattori, K. Takemaru, and Y. Miki Synlett 2011 1563
13. H. Hamamoto, H. Umemoto, M. Umemoto, C. Ohta, M. Dohshita, and Y. Miki Synlett 2010 2593
14. Y. Yamamoto, Y. Takahama, M. Shimizua, A. Ohara, A. Miyawaki, and K. Tomioka Tetrahedron Lett. 54 2013 4313
15. D.C. Fabry, M. Stodulski, S. Hoerner, and T. Gulder Chem. - Eur. J. 18 2012 10834
16. P. Pandit, K.S. Gayen, S. Khamarui, N. Chatterjee, and D.K. Maiti Chem. Commun. 2011 6933
17. L. Yu, L. Ren, R. Yi, Y. Wu, T. Chen, and R. Guo Synlett 2011 579
18. S. Sanjaya, and S. Chiba Tetrahedron 67 2011 590
19. P. Katrun, S. Chiampanichayakul, K. Korworapan, M. Pohmakotr, V. Reutrakul, T. Jaipetch, and C. Kuhakarn Eur. J. Org. Chem. 2010 5633
20. T. Wu, G. Yin, and G. Liu J. Am. Chem. Soc. 131 2009 16355
21. For a recent example, see: K.B. McMurtrey, J.M. Racowski, and M.S. Sanford Org. Lett. 14 2012 4094
22. S. Nocquet-Thibault, P. Retailleau, K. Cariou, and R.H. Dodd Org. Lett. 15 2013 1842
23. M. Nakanishi, C. Minard, K. Cariou, P. Retailleau, and R.H. Dodd Org. Lett. 13 2011 5792
24. For a review on iminoiodanes, see: P. Dauban, and R.H. Dodd Synlett 2003 1571
25. For an example of the use of iminoiodanes as surrogates for other hypervalent λ3-iodanes, see: S. Lee, and D.W.C. MacMillan Tetrahedron 62 2006 11413
26. N. Winterton Green Chem. 2 2000 173
27. K. Naumann J. Prakt. Chem. 341 1999 417
28. J.R. Mercer, E.E. Knaus, and L.I. Wiebe J. Med. Chem. 30 1987 670 tert-butyl-hypochlorite
29. K. Satake, M. Kimura, and S. Morosawa Chem. Lett. 1983 145 N-chlorosuccinimide
30. R. Kumar, D. Kumar, and A.K. Prasad Indian J. Chem. B 51 2012 1123
31. M.A. Ciufolini, and Q. Dong Chem. Commun. 1996 881
32. D. Viña, E. Quezada, L. Santana, and E. Uriarte Tetrahedron 62 2006 9949
33. M.R.P. Norton Matos, C.A. Afonso, and R.A. Batey Tetrahedron 61 2001 1221
34. M.R.P. Norton Matos, C.A.M. Afonso, T. McGarvey, P. Lee, and R.A. Batey Tetrahedron Lett. 40 1999 9189
35. M. Tadesse, J. Svenson, M. Jaspars, M.B. Strøm, M.H. Abdelrahman, J.H. Andersen, E. Hansen, P.E. Kristiansen, K. Stensvåg, and T. Haug Tetrahedron Lett. 52 2011 1804
36. M. Tadesse, M.B. Strøm, J. Svenson, M. Jaspars, B.F. Milne, V. Tørfoss, J.H. Andersen, E. Hansen, K. Stensvåg, and T. Haug Org. Lett. 12 2010 4752
37. CCDC 978123 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
38. R.M. Moriarty J. Org. Chem. 70 2005 2893
39. B.C. Schardt, and C.L. Hill Inorg. Chem. 22 1983 1563
40. M.S. Yusubov, R.J. Yusubova, V.D. Filiminov, and K.-W. Chi Synth. Commun. 34 2004 443
41. 2for the chlorination of alkenes see
42. L. Liu, D. Zhang-Negrerie, Y. Du, and K. Zhao Org. Lett. 16 2014 436
43. 3combination in ethanol; ethoxychlorination product 3b was indeed obtained with similar, albeit slightly lower, yield and diastereoselectivity
44. 2is used: W. Salamant, and C. Hulme Tetrahedron Lett. 47 2006 605
45. L.F. Silva Jr., R.S. Vasconcelos, and N.P. Lopes Int. J. Mass Spectrom. 276 2008 24
46. L.F. Silva Jr., and N.P. Lopes Tetrahedron Lett. 46 2005 6023
47. J.W. Sam, X.J. Tang, R.S. Magliozzo, and J. Peisach J. Am. Chem. Soc. 117 1995 1012
48. Here BHT did not react in any visible way. However, reactions involving BHT in the presence of DIB and a nucleophile have been reported when HFIP was used as the solvent, see: K.C. Guérard, C. Sabot, L. Racicot, and S. Canesi J. Org. Chem. 74 2009 2039
49. P. Magnus, J. Lacour, P.A. Evans, M.B. Roe, and C. Hulme J. Am. Chem. Soc. 118 1996 3406
50. For a recent example of difunctionalisation of alkenes with a hypervalent iodine reagent and TEMPONa, see: B. Zhang, and A. Studer Org. Lett. 15 2013 4548 see also Ref. 23
51. P.B. Thorat, B.Y. Bhong, and N.N. Karade Synlett 2013 2061
52. M. Barbazanges, C. Meyer, J. Cossy, and P. Turner Chem. - Eur. J. 17 2011 4480