Deprotonative metalation of aromatic compounds using mixed lithium-iron combinations

Tetrahedron

Volumn 68, Issue 14, 2012, Pages 3063-3073

  Nagaradja, Elisabeth ^a   Chevallier, Floris ^a   Roisnel, Thierry ^a   Jouikov, Viatcheslav ^a   Mongin, Florence ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Aromatic compounds; Bimetallic bases; Deprotonative metalation; Iron; Lithium

Indexed keywords

2 FLUOROPYRIDINE; 2 METHOXYPYRIDINE; 2,4 DIMETHOXYPYRIMIDINE; 2,6 DIMETHOXYPYRIDINE; 3,4,5 TRIMETHOXYBENZALDEHYDE; ALLYL BROMIDE; ANISOLE; AROMATIC COMPOUND; BENZALDEHYDE DERIVATIVE; BENZENECARBONYL CHLORIDE; BENZOPHENONE; BENZYL BROMIDE; BROMINE DERIVATIVE; CHLORIDE; DISULFIDE; IODINE; IRON; LITHIUM; METHYL IODIDE; PYRIDINE DERIVATIVE; TETRAMETHYLTHIURAM DISULPHIDE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL;

EID: 84858704222     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.019     Document Type: Article

References (62)

1. H.W. Gschwend, and H.R. Rodriguez Org. React. 26 1979 1 360
2. P. Beak, and V. Snieckus Acc. Chem. Res. 15 1982 306 312
3. V. Snieckus Chem. Rev. 90 1990 879 933
4. T.G. Gant, and A.I. Meyers Tetrahedron 50 1994 2297 2360
5. M. Schlosser M. Schlosser, Organometallics in Synthesis 2nd ed. 2002 Wiley Lausanne (Switzerland) Chapter I
6. M. Schlosser Pure Appl. Chem. 60 1988 1627 1634
7. L. Lochmann Eur. J. Inorg. Chem. 2000 1115 1126
8. P.C. Gros, and Y. Fort Eur. J. Org. Chem. 2009 4199 4209 and references cited therein
9. P.C. Gros, and Y. Fort Curr. Org. Chem. 15 2011 2329 2339
10. R.E. Mulvey Organometallics 25 2006 1060 1075
11. R.E. Mulvey, F. Mongin, M. Uchiyama, and Y. Kondo Angew. Chem., Int. Ed. 46 2007 3802 3824
12. R.E. Mulvey Acc. Chem. Res. 42 2009 743 755
13. B. Haag, M. Mosrin, H. Ila, V. Malakhov, and P. Knochel Angew. Chem., Int. Ed. 50 2011 9794 9824
14. F. Mongin, and M. Uchiyama Curr. Org. Chem. 15 2011 2340 2361
15. P. Alborés, L.M. Carrella, W. Clegg, P. García- Álvarez, A.R. Kennedy, J. Klett, R.E. Mulvey, E. Rentschler, and L. Russo Angew. Chem., Int. Ed. 48 2009 3317 3321
16. S.H. Wunderlich, and P. Knochel Angew. Chem., Int. Ed. 48 2009 9717 9720
17. S.H. Wunderlich, T. Bresser, C. Dunst, G. Monzon, and P. Knochel Synthesis 2010 2670 2678
18. A. Seggio, M.I. Lannou, F. Chevallier, D. Nobuto, M. Uchiyama, S. Golhen, T. Roisnel, and F. Mongin Chem. - Eur. J. 13 2007 9982 9989
19. A. Seggio, F. Chevallier, M. Vaultier, and F. Mongin J. Org. Chem. 72 2007 6602 6605
20. J.M. L'Helgoual'ch, A. Seggio, F. Chevallier, M. Yonehara, E. Jeanneau, M. Uchiyama, and F. Mongin J. Org. Chem. 73 2008 177 183
21. K. Snégaroff, S. Komagawa, F. Chevallier, P.C. Gros, S. Golhen, T. Roisnel, M. Uchiyama, and F. Mongin Chem. - Eur. J. 16 2010 8191 8201
22. G. Dayaker, A. Sreeshailam, F. Chevallier, T. Roisnel, P. Radha Krishna, and F. Mongin Chem. Commun. 2010 2862 2864
23. F. Chevallier, Y.S. Halauko, C. Pecceu, I.F. Nassar, T.U. Dam, T. Roisnel, V.E. Matulis, O.A. Ivashkevich, and F. Mongin Org. Biomol. Chem. 2011 4671 4684
24. J.M. L'Helgoual'ch, G. Bentabed-Ababsa, F. Chevallier, M. Yonehara, M. Uchiyama, A. Derdour, and F. Mongin Chem. Commun. 2008 5375 5377
25. J.M. L'Helgoual'ch, G. Bentabed-Ababsa, F. Chevallier, A. Derdour, and F. Mongin Synthesis 2008 4033 4035
26. G. Bentabed-Ababsa, F. Blanco, A. Derdour, F. Mongin, F. Trécourt, G. Queguiner, R. Ballesteros, and B. Abarca J. Org. Chem. 74 2009 163 169
27. K. Snégaroff, F. Lassagne, G. Bentabed-Ababsa, E. Nassar, S. Cheikh Sid Ely, S. Hesse, E. Perspicace, A. Derdour, and F. Mongin Org. Biomol. Chem. 7 2009 4782 4788
28. K. Snégaroff, J.M. L'Helgoual'ch, G. Bentabed-Ababsa, T.T. Nguyen, F. Chevallier, M. Yonehara, M. Uchiyama, A. Derdour, and F. Mongin Chem. - Eur. J. 15 2009 10280 10290
29. G. Bentabed-Ababsa, S. Cheikh Sid Ely, S. Hesse, E. Nassar, F. Chevallier, T.T. Nguyen, A. Derdour, and F. Mongin J. Org. Chem. 75 2010 839 847
30. K. Snégaroff, S. Komagawa, M. Yonehara, F. Chevallier, P.C. Gros, M. Uchiyama, and F. Mongin J. Org. Chem. 75 2010 3117 3120
31. A. Sreeshailam, G. Dayaker, F. Chevallier, T. Roisnel, P. Radha Krishna, and F. Mongin Eur. J. Org. Chem. 2011 3715 3718
32. T.T. Nguyen, F. Chevallier, V. Jouikov, and F. Mongin Tetrahedron Lett. 50 2009 6787 6790
33. T.T. Nguyen, N. Marquise, F. Chevallier, and F. Mongin Chem. - Eur. J. 17 2011 10405 10416
34. K. Snégaroff, T.T. Nguyen, N. Marquise, Y.S. Halauko, P.J. Harford, T. Roisnel, V.E. Matulis, O.A. Ivashkevich, F. Chevallier, A.E.H. Wheatley, P.C. Gros, and F. Mongin Chem. - Eur. J. 17 2011 13284 13297
35. G. Dayaker, F. Chevallier, P.C. Gros, and F. Mongin Tetrahedron 66 2010 8904 8910
36. T. Kauffmann, B. Laarmann, D. Menges, K.U. Voss, and D. Wingbermuehle Tetrahedron Lett. 31 1990 507 510
37. T. Kauffmann, B. Laarmann, D. Menges, and G. Neiteler Chem. Ber. 125 1992 163 169
38. H.J. Spiegl, G. Groh, and H.J. Berthold Z. Anorg. Allg. Chem. 398 1973 225 230
39. B. Scheiper, M. Bonnekessel, H. Krause, and A. Fürstner J. Org. Chem. 69 2004 3943 3949
40. A. Fürstner, H. Krause, and C.W. Lehmann Angew. Chem., Int. Ed. 45 2006 440 444
41. T.J.J. Sciarone, C.A. Nijhuis, A. Meetsma, and B. Hessen Dalton Trans. 2006 4896 4904
42. S.A. Sulway, D. Collison, J.J.W. McDouall, F. Tuna, and R.A. Layfield Inorg. Chem. 50 2011 2521 2526
43. D.R. Armstrong, P. Garcia-Alvarez, A.R. Kennedy, R.E. Mulvey, and J.A. Parkinson Angew. Chem., Int. Ed. 49 2010 3185 3188
44. G. Queguiner, F. Marsais, V. Snieckus, and J. Epsztajn Adv. Heterocycl. Chem. 52 1991 187 304
45. F. Mongin, and G. Queguiner Tetrahedron 57 2001 4059 4090
46. M. Schlosser, and F. Mongin Chem. Soc. Rev. 36 2007 1161 1172
47. T. Kauffmann Angew. Chem., Int. Ed. 35 1996 386 403
48. D. Occhialini, J.S. Kristensen, K. Daasbjerg, and H. Lund Acta Chem. Scand. 46 1992 474 481
49. C.P. Andrieux, I. Gallardo, and J.M. Savéant J. Am. Chem. Soc. 111 1989 1620 1626
50. A.M. Sukhotin Handbook of Electrochemistry 1981 Khimia Leningrad 488
51. M.T. Reetz, and S. Stanchev J. Chem. Soc., Chem. Commun. 1993 328 330
52. E.C. Ashby, and T.L. Wiesemann J. Am. Chem. Soc. 96 1974 7117 7119
53. E.C. Ashby, I.G. Lopp, and J.D. Buhler J. Am. Chem. Soc. 97 1975 1964 1966
54. T. Kauffmann, A. Hülsduenker, D. Menges, H. Nienaber, L. Rethmeier, S. Robbe, D. Scherler, J. Schricke, and D. Wingbermühle Tetrahedron Lett. 31 1990 1553 1556
55. T. Kauffmann, G. Hopp, B. Laarmann, D. Stegemann, and D. Wingbermuehle Tetrahedron Lett. 31 1990 511 514
56. T. Kauffmann, K.U. Voss, and G. Neiteler Chem. Ber. 126 1993 1453 1459
57. M. Nakamura, K. Matsuo, S. Ito, and E. Nakamura J. Am. Chem. Soc. 126 2004 3686 3687
58. R.B. Bedford, M. Betham, D.W. Bruce, A.A. Danopoulos, R.M. Frost, and M. Hird J. Org. Chem. 71 2006 1104 1110
59. G. Cahiez, V. Habiak, C. Duplais, and A. Moyeux Angew. Chem., Int. Ed. 46 2007 4364 4366
60. P. Anbarasan, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 49 2010 2219 2222
61. P. Gros, Y. Fort, and P. Caubre J. Chem. Soc., Perkin Trans. 1 1998 1685 1690
62. K. Suzawa, M. Ueno, A.E.H. Wheatley, and Y. Kondo Chem. Commun. 2006 4850 4852