Ligand-free copper(I)-catalysed intramolecular direct C–H functionalization of azoles

Organic and Biomolecular Chemistry

Volumn 8, Issue 4, 2010, Pages 841-845

  Barbero, Nekane ^a   SanMartin, Raul ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950325476     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b916549e     Document Type: Article

References (69)

1. For some recent reports, see: D. Alberico M. E. Scott M. Lautens Chem. Rev. 2007 107 174-238.
2. K. Godula D. Sames Science 2006 312 67-72.
3. F. Kakiuchi N. Chatani Adv. Synth. Catal. 2003 345 1077-1101.
4. V. Ritleng C. Sirlin M. Pfeffer Chem. Rev. 2002 102 1731-1769.
5. J. Hassan M. Sévignon C. Gozzi E. Schulz M. Lemaire, M. Chem. Rev. 2002 102 1359-1469.
6. G. Dyker Angew. Chem., Int. Ed. 1999 38 1698-1712.
7. I. V. Seregin V. Gevorgyan Chem. Soc. Rev. 2007 36 1173-1193.
8. M. Miura M. Nomura Top. Curr. Chem. 2002 219 211-241.
9. C. A. Zificsak D. J. Hlasta Tetrahedron 2004 60 8991-9016.
10. R. G. Bergman Nature 2007 446 391-393.
11. M. S. Chen M. S. White Science 2007 318 783-787.
12. A. R. Dick M. S. Sanford Tetrahedron 2006 62 2439-2463 and references cited therein.
13. L. Ackermann A. Althammer R. Born Tetrahedron 2008 64 6115-6124.
14. J. C. Lewis S. H. Wiedemann R. G. Bergman J. A. Ellman Org. Lett. 2004 6 35-38.
15. X. Chen X.-S. Hao C. E. Goodhue J.-Q. Yu J. Am. Chem. Soc. 2006 128 6790-6791.
16. C. H. Jun H. Lee J. B. Hong J. Org. Chem. 1997 62 1200-1201.
17. C. P. Lenges M. Brookhart J. Am. Chem. Soc. 1999 121 6616-6623.
18. R. K. Thalji K. A. Ahrendt R. G. Bergman J. A. Ellman J. Am. Chem. Soc. 2001 123 9692-9693.
19. L. Ackermann, Top. Organomet. Chem., N. Chatani, Ed.; Springer: Berlin, Heidelberg, New York, NY, 2007, Vol. 24, pp 35–60.
20. Ackermann and co-workers have reported impressive palladium- and rhodium-catalysed direct arylation methodologies employing the less reactive aryl bromides, chlorides, tosylates and mesylates as electrophiles via C–H functionalization. See: L. Ackermann R. Vicente A. Althammer, A. Org. Lett. 2008 10 2299-2302.
21. L. Ackermann R. Born P. Álvarez-Bercedo Angew. Chem., Int. Ed. 2007 46 6364-6367.
22. L. Ackermann A. Althammer R. Born Angew. Chem., Int. Ed. 2006 45 2619-2622.
23. L. Ackermann A. Althammer S. Fenner Angew. Chem., Int. Ed. 2009 48 201-204.
24. H.-Q. Do R. M. K. Khan O. Daugulis J. Am. Chem. Soc. 2008 130 15185-15192.
25. H.-Q. Do O. Daugulis J. Am. Chem. Soc. 2007 129 12404-12405.
26. T. Yoshizumi H. Tsurugi T. Satoh M. Miura Tetrahedron Lett. 2008 49 1598-1600.
27. A. K. Verma T. Kesharwani J. Singh V. Tandon R. C. Larock Angew. Chem., Int. Ed. 2009 48 1138-1143.
28. S. Ueda H. Nagasawa Angew. Chem., Int. Ed. 2008 47 6411-6413.
29. S. Ueda H. Nagasawa J. Org. Chem. 2009 74 4272-4277.
30. R. J. Phipps N. P. Grimster M. J. Gaunt J. Am. Chem. Soc. 2008 130 8172-8174.
31. I. Ban T. Sudo T. Taniguchi K. Itami Org. Lett. 2008 10 3607-3609.
32. H.-Q. Do O. Daugulis J. Am. Chem. Soc. 2008 130 1128-1129.
33. G. Brasche S. L. Buchwald Angew. Chem., Int. Ed. 2008 47 1932-1934.
34. T. Kawano T. Yoshizumi K. Hirano T. Satoh M. Miura Org. Lett. 2009 11 3072-3075.
35. T. Yoshizumi T. Satoh K. Hirano D. Matsuo A. Orita J. Otera M. Miura Tetrahedron Lett. 2009 50 3273-3276.
36. M. Carril R. SanMartin E. Domínguez Chem. Soc. Rev. 2008 37 639-647 and references cited therein.
37. N. Barbero R. SanMartin E. Domínguez Tetrahedron 2008 64 7283-7288.
38. N. Barbero R. SanMartin E. Domínguez Green Chem. 2009 11 830-836.
39. N. Barbero Carril M. R. SanMartin E. Domínguez Tetrahedron 2007 63 10425-10432.
40. N. Barbero R. SanMartin E. Domínguez Tetrahedron Lett. 2009 50 2129-2131.
41. For some recent reviews, see: V. V. Lyaskovskyy Z. V. Voitenko V. A. Kovtunenko Chem. Heterocycl. Compd. 2007 43 253-276 and references cited therein.
42. Z. V. Voitenko T. V. Egorova V. A. Kovtunenko Chem. Heterocycl. Compd. 2002 38 1019-1039 and references cited therein.
43. S. K. Meegalla G. J. Stevens C. A. McQueen A. Y. Chen C. Yu L. F. Liu L. R. Barrows E. J. LaVoie J. Med. Chem. 1994 37 3434-3439.
44. Their potential activity as antibacterial, antitubercular and bronchodilator has also been evaluated, see: B. P. V. Lingaiah T. Yakaiah P. S. Rao B. Narsaiah Heterocycles 2005 65 2329-2337 and references cited therein.
45. K. M. Patel V. H. Patel M. P. Patel R. G. Patel Dyes Pigm. 2002 55 53-58.
46. A. P. Thomas C. P. Allott K. H. Gibson J. S. Major B. B. Masek A. A. Oldham A. H. Ratcliffe D. A. Roberts S. T. Russell D. A. Thomason J. Med. Chem. 1992 35 877-885.
47. S. Pivsa-Art T. Satoh Y. Kawamura M. Miura M. Nomura Bull. Chem. Soc. Jpn. 1998 71 467-473.
48. F. Besselièvre S. Piguel F. Mahuteau-Betzer D. S. Grierson Org. Lett. 2008 10 4029-4032.
49. For some recent examples on the use of benzotriazole, see: A. K. Verma J. Singh V. K. Sankar R. Chaudhary R. Chandra Tetrahedron Lett. 2007 48 4207-4210.
50. A. K. Verma T. Kesharwani J. Singh V. Tandon R. C. Larock Angew. Chem., Int. Ed. 2009 48 1138-1143.
51. For an example on the use of benzoimidazole-type ligands, see: V. O. Rodionov S. I. Presolski S. Gardinier Y.-H. Lim M. G. Finn J. Am. Chem. Soc. 2007 129 12696-12704.
52. During the development of this work You et al. reported the direct arylation of several heterocycles with the less reactive aryl bromides. See: D. Zhao W. Wang F. Yang J. Lan L. Yang G. Gao J. You Angew. Chem., Int. Ed. 2009 48 3296-3300.
53. R. Sanz J. M. Ignacio M. P. Castroviejo F. J. Fañanas Arkivoc 2007 84-91.
54. We subjected the mixture of regioisomers to the optimised cyclised conditions, but no product formation was observed.
55. For an alternative synthesis of 5H-imidazo[2,1-a]isoindole 2c based on palladium catalysis, see: R. Marcia de Figueiredo S. Thoret C. Huet J. Dubois Synthesis 2007 529-540.
56. For a recently reported palladium-catalysed synthesis of isoindolo[2,1-a]benzimidazole 2a, see: K. C. Majumdar P. Debnath A. Taher A. K. Pal Can. J. Chem. 2008 86 325-332.
57. Some examples of palladium- and rhodium-catalysed purine arylation can be found in: K. L. Tan R. G. Bergman J. A. Ellman J. Am. Chem. Soc. 2002 124 13964-13965.
58. K. L. Tan S. Park J. A. Ellman R. G. Bergman J. Org. Chem. 2004 69 7329-7335 To the best of our knowledge, the 4-azabenzimidazole framework has never been directly arylated through a metal-catalysed C–H functionalization.
59. S. V. Goldstein, W. G. Stirtan, and B. A. Sherer, Patent US 2001, US 6242461.
60. T. Gungor A. Fouquet J. M. Teulon D. Provost M. Cazes A. Cloarec J. Med. Chem. 1992 35 4455-4463.
61. For a recent example, see: A. A. O. Sarhan C. Bolm Chem. Soc. Rev. 2009 38 2730-2744.
62. For some relevant reviews of copper-catalysed coupling reactions and the mechanism involved, see: G. Evano N. Blanchard M. Toumi Chem. Rev. 2008 108 3054-3131.
63. S. V. Ley A. W. Thomas Angew. Chem., Int. Ed. 2003 42 5400-5449.
64. I. P. Beletskaya A. V. Cheprakov Coord. Chem. Rev. 2004 248 2337-2369.
65. J. Hassan M. Svignon C. Gozzi E. Schulz M. Lemaire Chem. Rev. 2002 102 1359-1470.
66. K. Kunz U. Scholz D. Ganzer Synlett 2003 2428-2439.
67. F. Monnier M. Taillefer Angew. Chem., Int. Ed. 2008 47 3096-3099.
68. A. R. Muci S. L. Buchwald Top. Curr. Chem. 2002 219 131-209.
69. N. Arai M. Takahashi M. Mitani A. Mori Synlett 2006 3170-3172.