A versatile synthesis of substituted benzimidazolium salts by an amination/ ring closure sequence

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2673-2675

  Rivas, Felix M ^a   Riaz, Uzma ^a   Giessert, Anthony ^a   Smulik, Jason A ^a   Diver, Steven T ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZIMIDAZOLE DERIVATIVE; FURAN DERIVATIVE; INORGANIC SALT; PYRAN DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CHEMISTRY; KINETICS; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

AMINES; BENZIMIDAZOLES; CRYSTALLOGRAPHY, X-RAY; FURANS; KINETICS; PYRANS; SALTS; THERMODYNAMICS;

EID: 0035940140     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016254m     Document Type: Article

References (56)

1. Recent review: Arduengo, A. J. Acc. Chem. Res. 1999, 32 (11), 913-921.
2. (a) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187.
3. (b) Bourissou, D.; Guerret, D.; Gabbaie, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
4. (c) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
5. (d) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416-2419.
6. (e) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
7. (f) Jafarpour, L.; Nolan, S. P. Organometallics 2000, 19, 2055-2057.
8. (g) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207.
9. (h) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790.
10. (i) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415.
11. (j) Lee, H. M.; Smith, D. C., Jr.; He, Z.; Stevens, E. D.; Yim C. S.; Nolan, S. P. Organometallics 2001, 20, 794-797.
12. (k) Fürstner, A.; Leitner, A. Synlett 2001, 290-292.
13. (l) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
14. (m) Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 343, 343-350.
15. (n) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 677-678, 70-80.
16. (o) Enders, D.; Gielen, H.; Raabe, G.; Runsink, J.; Teles, J. H. Chem. Ber. 1996, 129, 1483-1488.
17. (p) Lee, H. M.; Jiang, T.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 1255-1258.
18. Enthalpy of binding to metals and chalcogens has been measured by calorimetry: (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 727, 2674-2678.
19. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P.; Capps, K. B.; Bauer, A.; Hoff, C. D. Inorg. Chem. 2000, 39, 1042-1045.
20. (c) Huang, J.; Jafarpour, L.; Hillier, A. C.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 2878-2882.
21. An alternative approach involves desulfurization of the thiourea: (a) Kuhn, N.; Kratz, T. Synthesis 1993, 561-562.
22. (b) Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609.
23. (c) Hahn, F. E.; Wittenbecher, L.; Van, D. L.; Fröhlich, R. Angew. Chem., Int. Ed. 2000, 39, 541-544.
24. (d) Kuhn, N.; Niquet, E.; Steimann, M.; Walker, I. Z. Naturforsch. B 1999, 54, 1181-1187.
25. (e) Karkhanis, D. W.; Field, L. Phos., Sulfur 1985, 22, 49-57.
26. (f) Arduengo, A. J.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J. Angew. Chem., Int. Ed. 1998, 37, 1963-1965.
27. (g) Faust, R.; Göbelt, B. Chem. Commun. 2000, 919-920.
28. (a) Herrmann, W. A.; Goossen, L. J.; Köcher. C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
29. (b) Herrmann, W. A.; Goossen, L. J.; Artus, G. R. J.; Köcher, C. Organometallics, 1997, 16, 1472-2477.
30. (c) Arduengo, A. J. U.S. Patent 5,077,414, 1991.
31. (d) Gridnev, A. A.; Mihaltseva, I. M. Synth. Commun. 1994, 24, 1547-1555.
32. (e) Arduengo, A. J.; Krafczyk, R.; Schmutzler, R. Tetrahedron, 1999, 55, 14523-14534.
33. (a) Saba, S.; Brescia, A.; Kaloustian, M. K. Tetrahedron Lett. 1991, 32, 5031-5034.
34. (b) Cabanal-Duvillard, I.; Mangeney, P. Tetrahedron Lett. 1999, 40, 3877-3880.
35. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
36. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750.
37. Direct alkylation of benzimidazole is possible but produces a mixture of enantiomers and diastereomers. Preparation of N-sec-phenethylbenzimidazole: Simonov, A. M.; Pozharskii, A. F. Zh. Obshch. Khim. 1964, 34, 1572-1574.
38. (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
39. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc 1996, 118, 7217-7218. Reviews:
40. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
41. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2047.
42. (e) Yang, B. H.; Buchwald S. L. J. Organomet. Chem. 1999, 576, 125-146.
43. (a) Witulski, B.; Senft, S.; Thum, A. Synlett 1998, 504-506.
44. (b) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1999, 40, 6393-6397.
45. (c) Rivas, F. M.; Riaz, U.; Diver, S. T. Tetrahedron: Asymmetry 2000, 11, 1703-1707.
46. Mechanistic work on the β-elimination pathway: (a) Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633.
47. (b) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458.
48. 4B salt, 7.03 ppm.
49. Phase transfer-catalyzed allylation of the benzophenone imine of glycine tert-butyl ester using catalyst 19 gave a 92% yield of monoallylated product of 31% ee. Further studies are in progress.
50. 6: Shi, Z.; Thummel, R. P. Tetrahedron Lett. 1994, 35, 33-36.
51. 2.
52. (a) Hahn, F. E.; Wittenbecher, L.; Boese, R.; Bläser, D. Chem. Eur. J. 1999, 5, 1931-1935.
53. (b) Liu, Y.; Lindner, P. E.; Lemal, D. M. J. Am. Chem. Soc. 1999, 121, 10626-10627.
54. (c) Arduengo, A. J.; Dias, R. H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
55. The nucleophilicity of 35 is akin to an enamine; however, the aromatic resonance contributor probably enhances the nucleophilicity of the enamine terminal carbon atom, (a) For relevant study reporting the methylation of an enamine similar to 35, see: Bourson, J. Bull. Soc. Chim. Fr. 1971, 3541-3547.
56. (b) Study of an imidazole-2-methylidene: Arduengo, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742-12749.