Imidazo[1,5-a]pyridin-3-ylidene/thioether mixed C/S ligands and complexes thereof

Organometallics

Volumn 26, Issue 10, 2007, Pages 2570-2578

  Roseblade, Stephen J ^a   Ros, Abel ^a   Monge, David ^b   Alcarazo, Manuel ^a   Álvarez, Eleuterio ^a   Lassaletta, José M ^a   Fernández, Rosario ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; COMPLEXATION; CYCLIZATION; LIGANDS; REACTION KINETICS; STEREOCHEMISTRY;

ASYMMETRIC INDUCTION; FUNCTIONALIZED SIDE CHAINS; SULFUR ATOM; THIOETHER;

ETHERS;

EID: 34249004974     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om070063r     Document Type: Article

References (69)

1. Sprinz, J.; Helmchen, U. tetrahedron Lett. 1993, 34, 1769.
2. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
3. Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
4. (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
5. (b) Hou, D. R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206, and references therein.
6. Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691.
7. (a) Bell, S.; Wũstenberg, B.; Kaiser, S.; Menges, F.; Netscher, T.; Pfaltz A. Science 2006, 311, 642.
8. (b) Pfaltz A.; Drury, W. J., III. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5723.
9. (c) Drury, W. J.; Zimmermann, N.; Keenan, M.; Hayashi, M.; Kaiser, S.; Goddard, R.; Pfaltz, A. Angew. Chem., Int. Ed. 2004, 43, 70.
10. (d) Black, A.; Brown, J. M.; Pichon, C. Chem. Commun. 2005, 5284, and references therein.
11. (a) Dai, W. M.; Yeung, K. K. Y.; Liu, J. T.; Zhang, Y.; Williams, I. D. Org. Lett. 2002, 4, 1615.
12. (b) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525.
13. (a) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
14. (b) Evans, D. A.; Michael, F. E.; Tedrow, J. S.; Campos, K. R. J. Am. Chem. Soc. 2003, 125, 3534.
15. (a) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 35, 1523.
16. (b) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895.
17. (c) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
18. (d) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254.
19. Arduengo, A., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
20. (a) Hermann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
21. (b) Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348.
22. (a) Öfele, K.; Hermann, W. A.; Mihalios, D.; Elison, M.; Herdtweck, E.; Scherer, W.; Mink, J. J. Organomet. Chem. 1993, 459, 177.
23. (b) Herrmann, W. A.; Öfele, K.; Elison, M.; Kühn, F. E.; Roesky, P. W. J. Organomet. Chem. 1994, 480, C7.
24. (a) Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
25. (b) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201.
26. (c) Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 2000, 19, 1194.
27. (d) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche M.; Herrmann, W. A.; Hieringer W.; Raudaschl-Sieber G. Chem.-Eur. J. 2000, 6, 1773.
28. (e) Huang, J.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370.
29. 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.
30. (b) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
31. First synthesis: Hermann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.
32. (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.
33. (b) Nanchen, S.; Pfaltz, A. Chem.-Eur. J. 2006, 12, 4550.
34. (a) Gade, L. H.; César, V.; Bellemín-Laponnaz, S. Angew. Chem., Int. Ed. 2004, 43, 1014.
35. (b) César, V; Bellemín-Laponnaz, S; Wadepohl, H; Gade, L. H. Chem.-Eur. J. 2005, 11, 2862.
36. Bonnet, L. C.; Douthwaite, R. E.: Kariuki, B. M. Organometallics 2003, 22, 4187.
37. Lee, K.-S.; Brown, M. K.; Hird, A. W.; Hoveyda A. H. J. Am. Chem. Soc. 2006, 128, 7182.
38. Van Veldhuizen, J. J.; Garber, S. B.; Kinsbury J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
39. Bappert, E.; Helmchen, G. Synlett 2004, 1789.
40. Nanchen, S.; Pfaltz, A. Helv. Chim. Acta 2006, 89, 1559.
41. Becht, J. M.; Bappert, E.; Helmchen, G. Adv. Synth. Catal. 2005, 347, 1495.
42. Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2006, 25, 5927.
43. (a) Seo, H.; Park, H.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618.
44. (b) Cabeza, J. A.; del Río, I.; Sánchez-Vega, M. G.; Suárez, M. Organometallics 2006, 25, 1831.
45. (c) Huynh, H. V.; Yeo, C. H.; Tan, G. K. Chem. Commun. 2006, 3833.
46. Alcarazo, M.; Roseblade, S. J.; Alonso, E.; Fernández, R.; Álvarez, E.; Lahoz, F. J.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242.
47. Ros, A.; Monge, D.; Alcarazo, M.; Álvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2006, 25, 6039.
48. Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta J. M. J. Am. Chem. Soc. 2005, 127, 3290.
49. The same type of carbenes were independently reported by Glorius and coworkers: Burstein, C.; Lehmann, C. W.; Glorius, F. Tetrahedron 2005, 61, 6207.
50. See also: Nonnenmacher, M.; Kunz, D.; Rominger, F.; Oeser, T. J. Organomet. Chem. 2005, 690, 5647.
51. Nonnenmacher, M.; Kunz, D.; Rominger, F.; Oeser, T. Chem. Commun. 2006, 1378.
52. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972.
53. Bower, J. D.; Ramaje, G. R. J. Chem. Soc. 1965, 2834.
54. For a review on the structure and dynamics of chiral allyl Pd(II) complexes see: Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35.
55. Recent review: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
56. Liu, J.; Chen, J.; Zhao, J.; Zhao, Y.; Li, L.; Zhang, H. Synthesis 2003, 2661.
57. (a) Yao, W.; Eisenstein, O.; Crabtree, R. H. Inorg. Chim. Acta 1997, 254, 105.
58. (b) Lewis, J. C.; Wu, J.; Bergman, R. G.; Ellman, J. A. Organometallics 2005, 24, 5737.
59. In one of the alkylation experiments to obtain alcohol 14 the temperature was accidentally raised and the intermediate aldehyde racemized partially. Therefore, the synthesis of the corresponding Pd catalysts led to a product contaminated with a small amount of the (S,S)-enantiomer. The crystallization of an enantiomerically impure sample of complex 23 afforded the crystalline racemate.
60. (a) Lee, C. K.; Lee, K. M.; Lin, I. J. B. Organometallics 2002, 21, 10.
61. (b) Chen, W.; Liu, F. J. Organomet. Chem. 2003, 673, 5.
62. (c) Ramírez, J.; Corberan, R.; Sanau, M.; Peris, E.; Fernández, E. Chem. Commun. 2005, 3056.
63. Bower, J. D.; Ramage, G. R. J. Chem. Soc. 1955, 2834.
64. (a) Inorg. Synth. 1972, 13, 55.
65. (b) Wayland, B. B.; Schramm, R. F. Inorg. Chem. 1969, 8, 971.
66. SAINT 6.02; Bruker-AXS, Inc.: Madison, WI 53711-5373, 1997-1999.
67. Sheldrick, G. SADABS; Bruker AXS, Inc.: Madison, WI, 1999.
68. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Polidori, G.; Spagna R. SIR2002: The program. J. Appl. Crystallogr. 2003, 36, 1103.
69. SHELXTL 6.14; Bruker AXS, Inc.: Madison, WI, 2000-2003.