Stereoselective synthesis of rhodium(I) 4-(dialkylamino)triazol-5-ylidene complexes

Organometallics

Volumn 27, Issue 18, 2008, Pages 4555-4564

  Ros, Abel ^a   Alcarazo, Manuel ^b   Iglesias Sigüenza, Javier ^a   Díez, Elena ^a   Álvarez, Eleuterio ^b   Fernández, Rosario ^a   Lassaletta, José M ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINES; CHEMICAL OXYGEN DEMAND; CHEMICAL REACTIONS; COMPLEXATION; HYDROCARBONS; RHODIUM; SALTS; STEREOCHEMISTRY; STEREOSELECTIVITY;

STEREO-SELECTIVE SYNTHESIS; SYNTHESIS OF; TRIAZOLIUM;

RHODIUM COMPOUNDS;

EID: 53849092064     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800533g     Document Type: Article

References (70)

1. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
2. (b) Nolan, S. P., Ed. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
3. (c) Glorius, F., Ed. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer: Heidelberg, Germany, 2007.
4. (d) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122.
5. The applications of chiral NHCs as ligands in asymmetric catalysis have been recently reviewed: (a) César, V.; Bellemín-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
6. (b) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
7. Bappert, E.; Helmchen, G. Synlett 2004, 1789.
8. (a) Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. V. J. Am. Chem. Soc. 2003, 125, 113.
9. (b) Nanchen, S.; Pfaltz, A. Helv. Chim. Acta 2006, 89, 1559.
10. (c) Nanchen, S.; Pfaltz, A. Chem. Eur. J. 2006, 12, 4550.
11. Becht, J. M.; Bappert, E.; Helmchen, G. Adv. Synth. Catal. 2005, 347, 1495.
12. (a) Bonnet, L. C.; Douthwaite, R. E.; Kariuki, B. M. Organometallics 2003, 22, 4187.
13. (b) Ros, A.; Monge, D.; Alcarazo, M.; Álvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2006, 25, 6039.
14. (c) Roseblade, S. J.; Ros, A.; Monge, D.; Alcarazo, M.; Álvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2007, 26, 2570.
15. (a) Lee, K.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182.
16. (b) Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416.
17. Van Veldhuizen, J. J.; Garber, S. B.; Kinsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
18. (a) Gade, L. H.; César, V.; Bellemín-Laponnaz, S. Angew. Chem., Int. Ed. 2004, 43, 1014.
19. (b) César, V.; Bellemín-Laponnaz, S.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2005, 11, 2862.
20. (c) Faller, J. W.; Fontaine, P. P. Organometallics 2006, 25, 5887.
21. (d) Herrmann, W. A.; Baskakov, D.; Herdtweck, E.; Hoffmann, S. D.; Bunlaksananusorn, T.; Rampf, F.; Rodefeld, L. Organometallics 2006, 25, 2449.
22. Alcarazo, M.; Roseblade, S. J.; Alonso, E.; Fernández, R.; Álvarez, E.; Lahoz, F. J.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242.
23. (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
24. (b) The same type of carbenes were independently reported by Glorius and co-workers: Burstein, C.; Uhmann, C. W.; Glorius, F. Tetrahedron 2005, 61, 6207.
25. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
26. For the use of chiral triazol-5-ylidenes as organocatalysts see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
27. (b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606, and references therein.
28. (c) Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520.
29. (d) He, M.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 418.
30. (e) Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S. Org. Lett. 2008, 10, 277.
31. (f) Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416.
32. (a) Enders, D.; Gielen, H.; Breuer, K. Molecules Online 1998, 2, 105.
33. (b) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 70, 617-618, and references cited therein.
34. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Uhmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236.
35. (d) Gnanamgari, D.; Moores, A.; Rajaseelan, E.; Crabtree, R. H. Organometallics 2007, 26, 1226.
36. Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437.
37. For a previous report on the synthesis and structure of achiral heteroatom-substituted mono- and bis-triazol-5-ylidenes see: (a) Alcarazo, M.; Fernández, R.; Álvarez, E.; Lassaletta, J. M. J. Organomet. Chem. 2005, 690, 5979.
38. Teles. J. H.; Melder, J.-P.; Ebel, K.; Schneider, R.; Gehrer, E.; Harder, W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv. Chim. Acta 1996, 79, 61.
39. Boyd, G. V.; Dando, S. R. J. Chem. Soc. 1970, 1397.
40. (a) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165.
41. (b) Taber, D. F.; Gorski, G. J.; Liable-Sands, L. M.; Rheingold, A. L. Tetrahedron Lett. 1997, 38, 6317.
42. (c) He, S.; Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 190.
43. (d) Fernández, R.; Ferrete, A.; Lassaletta, J. M.; Liera, J. M.; Monge, A. Angew. Chem. Int. Ed. 2000, 39, 2893.
44. (e) Fernández, R.; Ferrete, A.; Lassaletta, J. M.; Llera, J. M.; Martín-Zamora, E. Angew. Chem.. Int. Ed. 2002, 42, 831.
45. (f) Alcarazo, M.; Fernandez, R.; Lassaletta, J. M. Chem. Commun. 2004, 298.
46. (g) Martín-Zamora, E.; Ferrete, A.; Llera, J. M.; Muñoz, J. M.; Pappalardo, R. R.; Fernandez, R.; Lassaletta, J. M. Chem. Eur. J. 2004, 10, 6111.
47. (h) Díez, E.; Fernandez, R.; Marqués-López, E.; Lassaletta, J. M. Org. Lett. 2004, 6, 2749.
48. (i) Sato, M.; Gunji, Y.; Ikeno, T.; Yamada, T. Chem. Lett. 2005, 34, 316.
49. (j) Ros, A.; Álvarez, E.; Dietrich. H. Synlett 2005, 2899.
50. (k) Prieto, A.; Simon, M.; Vázquez, J.; Álvarez, E.; Fernández, R.; Lassaletta, J. M. Synthesis 2006, 540.
51. (l) Marqués-López, E.; Martín-Zamora, E.; Díez, E.; Fernández, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2008, 2960.
52. Castellano, S.; Stefancich, G.; Musiu, C.; La Colla, P. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 299.
53. Bartlett, R. K.; Humphrey, I. R. J. Chem. Soc. C 1967, 1664.
54. The high steric bulk inhibits the C-Rh bond rotation even for the less hindered complex 21. For related examples of hindered Rh-C(CNH) bonds, see: (a) Ku, R. Z.; Huang, J. C.; Cho, J. Y.; Kiang, F. M.; Reddy, K. R.; Chen, Y. C.; Lee, K. J.; Lee, G. H.; Peng, S. M.; Liu, S. T. Organometallics 1999, 18, 2145.
55. (b) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. J. J. Organomet. Chem. 1997, 547, 357.
56. (c) Westkamp, T.; Schattenmann, W. C.; Spiegler, M. J.; Herrmann, W. A. Angew. Chem., Int. Ed 1998, 37, 2490.
57. (d) Özdemir, I.; Yigit, B.; Çetinkaya, B.; Ülkü, D.; Tahir, M. N.; Arici, C. J. Organomet. Chem. 2001, 633, 27.
58. (e) Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
59. (f) See ref 9c,d and 14a,c.
60. 6b
61. The asymmetric unit of the structure is formed by four symmetrically independent Perchlorate salts, with similar geometries for the triazolium cations. Each pair of cations shows strong face-to-face aromaticstacking interactions between the 1-phenyl rings of both triazoliums and edge-to-face interactions between the 1-phenyl ring of one triazolium and a phenyl ring of the Pyrrolidin-1-yl group of another triazolium cation.
62. The separation of the pure major isomer confirms the configurational stability of the complex, as no trace of the minor isomer was observed after chromatography.
63. (a) Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219.
64. (b) Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
65. (c) Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437.
66. (a) Chianese, A. R.; Crabtree, R. H. Organometallics 2005, 24, 4432.
67. (b) Enders, D.; Gielen, H.; Runsink, J.; Breuer, K.; Brode, S.; Boehn, K. Eur. J. Inorg. Chem. 1998, 913.
68. Duan, W. L.; Shi, M.; Rong, G. B. Chem. Commun. 2003, 2916.
69. Enders, D.; Kipphardt, H.; Gerdes, P.; Breña-Valle, L. J.; Bhushan, V. Bull. Soc. Chim. Belg. 1988, 97, 691.
70. Evans, D. A.; Michael, F. E.; Tedrow, J. S.; Campos, K. R. J. Am. Chem. Soc. 2003, 125, 3534.