Palladium-catalysed direct arylations of NH-free pyrrole and N-tosylpyrrole with aryl bromides

Tetrahedron Letters

Volumn 53, Issue 5, 2012, Pages 509-513

  Bheeter, Charles Beromeo ^a   Bera, Jitendra K ^b   Doucet, Henri ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Aryl bromides; C H activation; Catalysis; Palladium; Pyrroles

Indexed keywords

ACETIC ACID; BROMIDE; HALIDE; N (PARA TOLUENESULFONYL)PYRROLE; N,N DIMETHYLACETAMIDE; NH FREE PYRROLE; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; BIOTRANSFORMATION; CATALYST; CHEMICAL MODIFICATION; CONTROLLED STUDY; CROSS COUPLING REACTION; NEGISHI REACTION; STEREOCHEMISTRY; STILLE REACTION; SUZUKI REACTION; SYNTHESIS; TOSYLATION;

EID: 84355166794     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.081     Document Type: Article

References (49)

1. R.A. Jones Pyrroles 1990 Wiley-Interscience New York
2. J.J. Li, and G.W. Gribble Palladium in Heterocyclic Chemistry 2000 Pergamon Amsterdam
3. A. Ohta, Y. Akita, T. Ohkuwa, M. Chiba, R. Fukunaga, A. Miyafuji, T. Nakata, N. Tani, and Y. Aoyagi Heterocycles 31 1990 1951 1958
4. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
5. T. Satoh, and M. Miura Chem. Lett. 36 2007 200 205
6. L.-C. Campeau, D.R. Stuart, and K. Fagnou Aldrichimica Acta 40 2007 35 41
7. I.V. Seregin, and V. Gevoryan Chem. Soc. Rev. 36 2007 1173 1193
8. B.-J. Li, S.-D. Yang, and Z.-J. Shi Synlett 2008 949 957
9. F. Bellina, and R. Rossi Tetrahedron 65 2009 10269 10310
10. L. Ackermann, R. Vincente, and A.R. Kapdi Angew. Chem., Int. Ed. 48 2009 9792 9826
11. J. Roger, A.L. Gottumukkala, and H. Doucet Chem. Cat. Chem. 2 2010 20 40
12. C. Fischmeister, and H. Doucet Green Chem. 13 2011 741 753
13. For selected recent examples of direct arylations from our laboratory: F. Derridj, J. Roger, F. Geneste, S. Djebbar, and H. Doucet J. Organomet. Chem. 694 2009 455 465
14. J. Roger, and H. Doucet Tetrahedron 65 2009 9772 9781
15. J.J. Dong, J. Roger, F. Požgan, and H. Doucet Green Chem. 11 2009 1832 1846
16. J.J. Dong, J. Roger, and H. Doucet Tetrahedron Lett. 50 2009 2778 2781
17. J. Roger, F. Požgan, and H. Doucet Green Chem. 11 2009 425 432
18. Y. Fall, C. Reynaud, H. Doucet, and M. Santelli Eur. J. Org. Chem. 2009 4041 4050
19. J. Roger, C. Verrier, R. Le Goff, C. Hoarau, and H. Doucet ChemSusChem 2 2009 951 956
20. M. Ionita, J. Roger, and H. Doucet ChemSusChem 3 2010 367 376
21. F. Derridj, J. Roger, S. Djebbar, and H. Doucet Org. Lett. 12 2010 4320 4323
22. J. Roger, F. Pozgan, and H. Doucet Adv. Synth. Catal. 352 2010 696 710
23. For recent examples of intermolecular direct arylations of N-alkyl- or N-arylpyrroles: B.B. Toure, B.S. Lane, and D. Sames Org. Lett. 8 2006 1979 1982
24. B. Liégaut, D. Lapointe, L. Caron, A. Vlassova, and K. Fagnou J. Org. Chem. 74 2009 1826 1834
25. J. Roger, and H. Doucet Adv. Synth. Catal. 351 2009 1977 1990
26. Y. Fall, H. Doucet, and M. Santelli ChemSusChem 2 2009 153 157
27. D.T. Gryko, O. Vakuliuk, D. Gryko, and B. Koszarna J. Org. Chem. 74 2009 9517 9520
28. B. Liegault, I. Petrov, S.I. Gorelsky, and K. Fagnou J. Org. Chem. 75 2010 1047 1060
29. O. Rene, and K. Fagnou Adv. Synth. Catal. 352 2010 2116 2120
30. E.T. Nadres, A. Lazareva, and O. Daugulis J. Org. Chem. 76 2011 471 483
31. O. Vakuliuk, B. Koszarna, and D.T. Gryko Adv. Synth. Catal. 353 2011 925 930
32. For selected examples of direct arylations of NH-free indoles: F. Bellina, S. Cauteruccio, and R. Rossi Eur. J. Org. Chem. 2006 1379 1382
33. F. Bellina, C. Calandri, S. Cauteruccio, and R. Rossi Tetrahedron 63 2007 1970 1980
34. L. Joucla, N. Batail, and L. Djakovitch Adv. Synth. Catal. 352 2010 2929 2936
35. For examples of direct arylations of pyrrolyl salts: L. Filippini, M. Gusmeroli, and P. Riva Tetrahedron Lett. 33 1992 1755 1758
36. R.D. Rieth, N.P. Mankad, E. Calimano, and J.P. Sadighi Org. Lett. 6 2004 3981 3983
37. D.L. Swartz, and A.L. Odom Organometallics 25 2006 6125 6133
38. For examples of palladium-catalysed direct arylations of NH-free pyrroles: Y. Aoyagi, A. Inoue, I. Koizumi, R. Hashimoto, K. Tokunaga, K. Gohma, J. Komatsu, K. Sekine, A. Miyafuji, J. Kunoh, R. Honma, Y. Akita, and A. Ohta Heterocycles 33 1992 257 272
39. M. Romero, Y. Harrak, J. Basset, L. Ginet, P. Constans, and M.D. Pujol Tetrahedron 62 2006 9010 9016
40. X. Wang, D.V. Gribkov, and D. Sames J. Org. Chem. 72 2007 1476 1479
41. F. Jafarpour, S. Rahiminejadan, and H. Hazrati J. Org. Chem. 75 2010 3109 3112
42. For an example of rhodium-catalysed direct arylations of a NH-free pyrrole: X. Wang, B.S. Lane, and D. Sames J. Am. Chem. Soc. 127 2005 4996 4997
43. For examples of iridium-catalysed direct arylations of N-tosylpyrrole: B. Join, T. Yamamoto, and K. Itami Angew. Chem., Int. Ed. 48 2009 3644 3647
44. For examples of palladium-catalysed intramolecular direct arylations of N-tosylpyrroles: L. Joucla, F. Popowycz, O. Lozach, L. Meijer, and B. Joseph Helv. Chim. Acta 90 2007 753 763
45. T. Kowada, S. Yamaguchi, H. Fujinaga, and K.-I. Ohe Tetrahedron 67 2011 3105 3110
46. For examples of deprotection of N-tosylpyrroles: B.A. Merrill, and E. LeGoff J. Org. Chem. 55 1990 2904 2908
47. R. Settambolo, R. Lazzaroni, T. Messeri, M. Mazzetti, and P. Salvadori J. Org. Chem. 58 1993 7899 7902
48. M. Feuerstein, H. Doucet, and M. Santelli Synlett 2001 1980 1982
49. M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli Synthesis 2004 1281 1289