Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a new family of stable annulated N-heterocyclic carbenes: Synthesis, reactivity, and their application in coordination chemistry and organocatalysis

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8256-8264

  Ma, Yajun ^a   Wei, Siping ^a   Lan, Jingbo ^a   Wang, Jingzhi ^a   Xie, Rugang ^a   You, Jingsong ^a  

^a China   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL PROPERTIES; CHEMICAL REACTIONS; CONDENSATION; CRYSTALLOGRAPHY; ELECTRONIC PROPERTIES; MASS SPECTROMETRY; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; REACTION KINETICS; SALTS; SILVER; SILVER COMPOUNDS; SUBSTITUTION REACTIONS; SULFUR; THIOUREAS; TOLUENE; UREA; X RAY CRYSTALLOGRAPHY;

ARYL SUBSTITUENTS; BENZOIN CONDENSATIONS; CARBENE; CARBENES; CATALYTIC ACTIVITIES; CATALYTIC SPECIES; CHEMICAL EQUATIONS; COORDINATION CHEMISTRIES; ELECTRONIC NATURES; ELEMENTAL SULFURS; ESI MASSES; GOOD YIELDS; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS; ROOM TEMPERATURES; SHARP CONTRASTS; SILVER COMPLEXES; TRANSESTERIFICATIONS; TRIAZOLE RINGS; TRIAZOLIUM; X-RAY CRYSTALLOGRAPHIES;

COORDINATION REACTIONS;

CARBENOID; COORDINATION COMPOUND; DIMER; FLUOROPHOSPHATE; HETEROCYCLIC COMPOUND; PYRIDINE DERIVATIVE; PYRIDO[1,2 A][1,2,4]TRIAZOL 3 YLIDENE DERIVATIVE; SILVER DERIVATIVE; SULFUR; THIOUREA; TOLUENE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; ESTERIFICATION; POLYMERIZATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS; METHANE; TRIAZOLES;

EID: 55249103121     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801349d     Document Type: Article

References (97)

1. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
2. Selected reviews: (a) Regitz, M. Angew. Chem., Int. Ed. 1996, 35, 725-728.
3. (b) Herrmann, W. A.; Köchter, C. Angew. Chem., Int. Ed. 1997, 36, 2162-2187.
4. (e) Arduengo, A. J., III Acc. Chem. Res. 1999, 32, 913-921.
5. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
6. (e) Dupont, J.; Spencer, J. Angew. Chem., Int. Ed. 2004, 43, 5296-5297.
7. (f) Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348-1352.
8. Selected recent reviews for metal complexes of carbenes and their application in transition metal catalysis: (a) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22.
9. (b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2001, 48, 1-59.
10. (c) Hermann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
11. (d) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636.
12. (e) Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978-4008.
13. (f) Tekavec, T. N.; Louie, J. Top. Organomet. Chem. 2007, 21, 159-192.
14. (g) Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
15. (h) Kunz, D. Angew. Chem., Int. Ed. 2007, 46, 3405-3408.
16. Selected recent reviews: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
17. (b) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326-1328.
18. (c) Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506-7510.
19. (d) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000.
20. (e) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655.
21. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130-5135.
22. (a) Alder, R. W.; Blake, M. E.; Borlotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. J. Chem. Commun. 1999, 241-242.
23. (b) Bazinet, P.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 13314-13315.
24. (c) Mayr, M.; Wurst, K.; Ongania, K.-H.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 1256-1266.
25. (d) Lloyd-Jones, G. C.; Alder, R. W.; Owen-Smith, G. J. J. Chem. Eur. J. 2006, 12, 5361-5375.
26. (e) Bazinet, P.; Ong, T.-G.; O'Brien, J. S.; Lavoie, N.; Bell, E.; Yap, G. P. A.; Korobkov, I.; Richeson, D. S. Organometallics 2007, 26, 2885-2895.
27. (a) Scarborough, C. C.; Grady, M. J. W.; Guzei, I. A.; Gandhi, B. A.; Bunel, E. E.; Stahl, S. S. Angew. Chem., Int. Ed. 2005, 44, 5269-5272.
28. (b) Rogers, M. M.; Wendlandt, J. E.; Guzei, I. A.; Stahl, S. S. Org. Lett. 2006, 8, 2257-2260.
29. Selected recent examples: (a) Merceron-Saffon, N.; Baceiredo, A.; Gornitzka, H.; Bertrand, G. Science 2003, 301, 1223-1225.
30. (b) Cattoën, X.; Gornitzka, H.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 1342-1343.
31. (c) Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437-2448.
32. (d) Lavallo, V.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2006, 312, 722-724.
33. (e) Marrot, S.; Kato, T.; Cossío, F. P.; Gornitzka, H.; Baceiredo, A. Angew. Chem., Int. Ed. 2006, 45, 7447-7450.
34. (f) Yao, Q.; Zabawa, M.; Woo, J.; Zheng, C. J. Am. Chem. Soc. 2007, 129, 3088-3089.
35. (g) Jazzar, R.; Dewhurst, R. D.; Bourg, J.-B.; Donnadieu, B.; Canac, Y.; Bertrand, G. Angew. Chem., Int. Ed. 2007, 46, 2899-2902.
36. (h) Anderson, D. R.; Lavallo, V.; O'Leary, D. J.; Bertrand, G.; Grubbs, R. H. Angew. Chem., Int. Ed. 2007, 46, 7262-7265.
37. Selected recent examples: (a) Hahn, F. E.; Wittenbecher, L.; Boese, R.; Bläser, D. Chem. Eur. J. 1999, 5, 1931-1935.
38. (b) Rivas, F. M.; Riaz, U.; Giessert, A.; Smulik, J. A.; Diver, S. T. Org. Lett. 2001, 3, 2673-2676.
39. (c) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690-3693.
40. (d) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195-15201.
41. (e) Arduengo, A. J., III; Tapu, D.; Marshall, W. J. J. Am. Chem. Soc. 2005, 127, 16400-16401.
42. (f) Saravanakumar, S.; Oprea, A. I.; Kindermann, M. K.; Jones, P. G.; Heinicke, J. Chem. Eur. J. 2006, 12, 3143-3154.
43. (g) Khramov, D. M.; Boydston, A. J.; Bielawski, C. W. Angew. Chem., Int. Ed. 2006, 45, 6186-6189.
44. (h) Huynh, H. V.; Han, Y.; Ho, J. H. H.; Tan, G. K. Organometallics 2006, 25, 3267-3274.
45. Weiss, R.; Reichel, S.; Handke, M.; Hampel, F. Angew. Chem., Int. Ed. 1998, 37, 344-347.
46. (a) Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernández, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290-3291.
47. (b) Burstein, C.; Lehmann, C. W.; Glorius, F. Tetrahedron 2005, 61, 6207-6217.
48. (c) Fürstner, A.; Alcarazo, M.; Krause, H.; Lehmann, C. W. J. Am. Chem. Soc. 2007, 129, 12676-12677.
49. Ullah, F.; Bajor, G.; Veszprémi, T.; Jones, P. G.; Heinicke, J. W. Angew. Chem., Int. Ed. 2007, 46, 2697-2700.
50. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. 1995, 34, 1021-1023.
51. (a) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. I 1998, 1891-1893.
52. (b) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745.
53. (c) Kerr, M. S.; Alaniz, J. R.; Rovis, T. J. Org. Chem. 2005, 70, 10135-10138.
54. (d) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463-1467.
55. (e) Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 13796-13797.
56. Freund, M.; Horst, F. Chem. Ber. 1895, 28, 944-945.
57. (a) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-8, 70-80.
58. (b) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951-961.
59. Enders, D.; Breuer, K.; Kallfass, U.; Balensiefer, T. Synthesis 2003, 1292-1295.
60. Walentowski, R.; Wanzlick, H.-W. Z. Naturforsch., B: Chem. Sci. 1970, 25, 1421-1423.
61. Becker, H. G. O.; Hoffmann, G.; Gwan, K. M.; Knüpfer, L. J. Prakt. Chem. 1988, 330, 325-337.
62. Alhaider, A. A.; Abdelkader, M. A.; Lien, E. J. J. Med. Chem. 1985, 28, 1394-1398.
63. (a) Cerri, V.; Frejaville, C.; Vila, F.; Allouche, A.; Gronchi, G., Tordo, P. J. Org. Chem. 1989, 54, 1447-1450.
64. (b) Shen, D.; Diele, S.; Pelzl, G.; Wirthb, I.; Tschierske, C. J. Mater. Chem. 1999, 9, 661-672.
65. (c) Li, J.; Wang, Y.; Sun, T. Huaxue Shiji 2002, 24, 292-293.
66. (d) Dougan, S. J.; Melchart, M.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2006, 45, 10882-10894.
67. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
68. (a) Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. 1997, 36, 2607-2609.
69. (b) Hahn, F. E.; Paas, M.; Van, D. L.; Frölich, R. Chem. Eur. J. 2005, 11, 5080-5085.
70. (a) Taton, T. A.; Chen, P. Angew. Chem., Int. Ed. 1996, 35, 1011-1013.
71. (b) Shi, Z.; Goulle, V.; Thummel, R. P. Tetrahedron Lett. 1996, 37, 2357-2360.
72. (c) Tormos, G. V.; Bakker, M. G.; Wang, P.; Lakshmikantham, M. V.; Cava, M. P.; Metzger, R. M. J. Am. Chem. Soc. 1995, 117, 8528-8535.
73. (d) Liu, Y.-F.; Lindner, P. E.; Lemal, D. M. J. Am. Chem. Soc. 1999, 121, 10626-10627.
74. (e) Schoenebeck, F.; Murphy, J. A.; Zhou, S.; Uenoyama, Y.; Miclo, Y.; Tuttle, T. J. Am. Chem. Soc. 2007, 129, 13368-13369.
75. (a) Hahn, F. E.; Paas, M.; Van, D. L.; Lügger, T. Angew. Chem., Int. Ed. 2003, 42, 5243-5246.
76. (b) Wolf, J.; Böhlmann, W.; Findeisen, M.; Gelbrich, T.; Hofmann, R-J.; Schulze, B. Angew. Chem., Int. Ed. 2007, 46, 3118-3121.
77. A review summarizing these findings on the dimerization behavior of N-heterocyclic carbenes: Alder, R. W.; Blake, M. E.; Chaker, L.; Harvey, J. N.; Paolini, F.; Schütz, J. Angew. Chem., Int. Ed. 2004, 43, 5896-5911.
78. Selected recent examples: (a) Ramírez, J.; Corberán, R.; Sanaú, M.; Peris, E.; Fernandez, E. Chem. Commun. 2005, 3056-3058.
79. (b) Lee, K.-S.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182-7184.
80. (c) Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 1097-1100.
81. (d) McKie, R.; Murphy, J. A.; Park, S. R.; Spicer, M. D.; Zhou, S.-Z. Angew. Chem., Int. Ed. 2007, 46, 6525-6528.
82. (a) Wang, X.; Liu, S.; Weng, L.-H.; Jin, G.-X. Organometallics 2006, 25, 3565-3569.
83. (b) Poyatos, M.; Maisse-François, A.; Bellemin-Laponnaz, S.; Gade, L. H. Organometallics 2006, 25, 2634-2641.
84. de Frémont, P.; Scott, N. M.; Stevens, E. D.; Ramnial, T.; Lightbody, O. C.; Macdonald, C. L. B.; Clyburne, J. A. C.; Abernethy, C. D.; Nolan, S. P. Organometallics 2005, 24, 6301-6309.
85. (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
86. (b) Diederich, F.; Lutter, H. D. J. Am. Chem. Soc. 1989, 111, 8438-8446.
87. (c) Chen, Y.-T.; Barletta, G. L.; Haghjoo, K.; Cheng, J. T.; Jordan, F. J. Org. Chem. 1994, 59, 7714-7722.
88. (d) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242.
89. (e) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124-5131.
90. (f) Dudding, T.; Houk, K. N. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5770-5775.
91. (a) Lemal, D. M.; Lovald, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518-2519.
92. (b) Castells, J.; López-Calahorra, F.; Domingo, L. J. Org. Chem. 1988, 53, 4433-4436.
93. (c) Castells, J.; Domingo, L.; López-Calahorra, F.; Martí, J. Tetrahedron Lett. 1993, 34, 517-520.
94. (d) López-Calahorra, F.; Rubires, R. Tetrahedron 1995, 51, 9713-9728.
95. (e) López-Calahorra, F.; Castro, E.; Ochoa, A.; Martí, J. Tetrahedron Lett. 1996, 37, 5019-5022.
96. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583-3586.
97. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587-3590.