Beyond click-chemistry: Transformation of azides with cyclopentadienyl ruthenium complexes

Organometallics

Volumn 30, Issue 12, 2011, Pages 3412-3418

  Risse, Julie ^a   Scopelliti, Rosario ^a   Severin, Kay ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,5-CYCLOOCTADIENE; BENZONITRILES; BENZYLIC; CATALYST PRECURSORS; CLICK CHEMISTRY; COUPLING REACTION; CYCLOPENTADIENYLS; HIGH SELECTIVITY; PRESENCE OF WATER; RU COMPLEXES; RUTHENIUM COMPLEXES; STOICHIOMETRIC REACTION; TETRAZENE;

ALDEHYDES; BENZENE; CATALYST SELECTIVITY; CHEMICAL BONDS; NITROGEN COMPOUNDS; OLEFINS; RUTHENIUM;

RUTHENIUM COMPOUNDS;

EID: 79959488079     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200295c     Document Type: Article

References (58)

1. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998-15999
2. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015
3. Hou, D.-R.; Kuan, T.-C.; Li, Y.-K.; Lee, R.; Huang, K.-W. Tetrahedron 2010, 66, 9415-9420
4. Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923-8930
5. Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337-5339
6. Majireck, M. M.; Weinreb, S. M. J. Org. Chem. 2006, 71, 8680-8683
7. Johansson, J. R.; Lincoln, P.; Nordén, B.; Kann, N. J. Org. Chem. 2011, 76, 2355-2359
8. For selected examples see: Montagu, A.; Roy, V.; Balzarini, J.; Snoeck, R.; Andrei, G.; Agrofoglio, L. A. Eur. J. Med. Chem. 2011, 46, 778-786
9. Tietze, D.; Tischler, M.; Voigt, S.; Imhof, D.; Ohlenschläger, O.; Görlach, M.; Buntkowsky, G. Chem.-Eur. J. 2010, 16, 7572-7578
10. Moumné, R.; Larue, V.; Seijo, B.; Lecourt, T.; Micouin, L.; Tisné, C. Org. Biomol. Chem. 2010, 8, 1154-1159
11. Takasu, K.; Azuma, T.; Takemoto, Y. Tetrahedron Lett. 2010, 51, 2737-2740
12. Van Poecke, S.; Negri, A.; Gago, F.; Van Daele, I.; Solaroli, N.; Karlsson, A.; Balzarini, J.; Van Calenbergh, S. J. Med. Chem. 2010, 53, 2902-2912
13. Kee, J.-M.; Villani, B.; Carpenter, L. R.; Muir, T. W. J. Am. Chem. Soc. 2010, 132, 14327-14329
14. Odlo, K.; Fournier-Dit-Chabert, J.; Ducki, S.; Gani, O. A. B. S. M.; Sylte, I.; Hansen, T. V. Bioorg. Med. Chem. 2010, 18, 6874-6885
15. Chemama, M.; Fonvielle, M.; Arthur, M.; Valéry, J.-M.; Etheve-Quelquejeu, M. Chem.-Eur. J. 2009, 15, 1929-1938
16. Nulwala, H.; Takizawa, K.; Odukale, A.; Khan, A.; Thibault, R. J.; Taft, B. R.; Lipshutz, B. H.; Hawker, C. J. Macromolecules 2009, 42, 6068-6074
17. Oppilliart, S.; Mousseau, G.; Zhang, L.; Jia, G.; Thuéry, P.; Rousseau, B.; Cintrat, J.-C. Tetrahedron 2007, 63, 8094-8098
18. Tam, A.; Arnold, U.; Soellner, M. B.; Raines, R. T. J. Am. Chem. Soc. 2007, 129, 12670-12671
19. Dutta, B.; Solari, E.; Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2007, 26, 4791-4799
20. Gauthier, S.; Solari, E.; Dutta, B.; Scopelliti, R.; Severin, K. Chem. Commun. 2007, 1837-1839
21. Dutta, B.; Curchod, B. F. E.; Campomanes, P.; Solari, E.; Scopelliti, R.; Rothlisberger, U.; Severin, K. Chem.-Eur. J. 2010, 16, 8400-8409
22. Dutta, B.; Scopelliti, R.; Severin, K. Organometallics 2008, 27, 423-429
23. Dutta, B.; Scolaro, C.; Scopelliti, R.; Dyson, P. J.; Severin, K. Organometallics 2008, 27, 1355-1357
24. Broggi, J.; Díez-González, S.; Petersen, J. L.; Berteina-Raboin, S.; Nolan, S. P.; Agrofoglio, L. A. Synthesis 2008, 1, 141-148
25. Chou, C.-H.; Chu, L.-T.; Chiu, S.-J.; Lee, C.-F.; She, Y.-T. Tetrahedron 2004, 60, 6581-6584
26. Abbiati, G.; Contini, A.; Nava, D.; Rossi, E. Tetrahedron 2009, 65, 4664-4670
27. Hunter, D. H.; Sim, S. K. Can. J. Chem. 1972, 50, 669-677
28. Chen, M.-H.; Chen, Z.; Song, B.-A; Bhadury, P. S.; Yang, S.; Cai, X.-J.; Hu, D.-Y.; Xue, W.; Zeng, S. J. Agric. Food. Chem. 2009, 57, 1383-1388
29. Long, N.; Cai, X.-J.; Song, B.-A.; Yang, S.; Chen, Z.; Bhadury, P. S.; Hu, D.-Y.; Jin, L.-H.; Xue, W. J. Agric. Food Chem. 2008, 56, 5242-5246
30. Hu, D.-Y.; Wan, Q.-Q.; Yang, S.; Song, B.-A.; Bhadury, P. S.; Jin, L.-H.; Yan, K.; Liu, F.; Chen, Z.; Xue, W. J. Agric. Food Chem. 2008, 56, 998-1001
31. Kaboudin, B.; Moradi, K. Tetrahedron Lett. 2005, 46, 2989-2991
32. Azizi, N.; Akbari, E.; Amiri, A. K.; Saidi, M. R. Tetrahedron Lett. 2008, 49, 6682-6684
33. Corey, E. J.; Kühnle, F. N. M. Tetrahedron Lett. 1997, 38, 8631-8634
34. Hunter, D. H.; Sim, S. K. Can. J. Chem. 1972, 50, 678-689
35. Busacca, C. A.; Bartholomeyzik, T.; Cheekoori, S.; Grinberg, N.; Lee, H.; Ma, S.; Saha, A.; Shen, S.; Senanayake, C. H. J. Org. Chem. 2008, 73, 9756-9761
36. Braddock, D. C.; Redmond, J. M.; Hermitage, S. A.; White, A. J. P. Adv. Synth. Catal. 2006, 348, 911-916
37. Williams, O. F.; Bailar, J. C., Jr. J. Am. Chem. Soc. 1959, 81, 4464-4469
38. Ramesha, A. R.; Bhat, S.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7682-7683
39. Tetrazene ligands can also coordinate as monoanionic radicals as observed for an Fe complex: Cowley, R. E.; Bill, E.; Neese, F.; Brennessel, W. W.; Holand, P. L. Inorg. Chem. 2009, 48, 4828-4836
40. Danopoulos, A. A.; Hay-Motherwell, R. S.; Wilkinson, G.; Cafferkey, S. M.; Sweet, T. K. N.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1997, 3177-3184
41. Danopoulos, A. A.; Wilkinson, G.; Sweet, T. K. N.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1996, 3771-3778
42. Attempts to obtain larger amounts of crystalline 3 failed, and further analyses (NMR, elemental analysis) were therefore not performed.
43. Albertin, G.; Antoniutti, S.; Castro, J. J. Organomet. Chem. 2010, 695, 574-579
44. Albertin, G.; Antoniutti, S.; Baldan, D.; Castro, J.; Garćia-Fontán, S. Inorg. Chem. 2008, 47, 742-748
45. Albertin, G.; Antoniutti, S.; Bacchi, A.; Celebrin, A.; Pelizzi, G.; Zanardo, G. Dalton Trans. 2007, 661-668
46. Maddani, M.; Prabhu, K. R. Tetrahedron Lett. 2008, 49, 4526-4530
47. Strain, H. H. J. Am. Chem. Soc. 1927, 49, 1558-1571
48. Levison, J. J.; Robinson, S. D. J. Chem. Soc. A 1970, 2947-2954
49. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274-278
50. Kölle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267-273
51. Hodson, E.; Simpson, S. J. Polyhedron 2004, 23, 2695-2707
52. La Placa, S. J.; Ibers, J. A. Inorg. Chem. 1965, 4, 778-783
53. Colombano, G.; Travelli, C.; Galli, U.; Caldarelli, A.; Chini, M. G.; Canonico, P. L.; Sorba, G.; Bifulco, G.; Tron, G. C.; Genazzani, A. A. J. Med. Chem. 2009, 53, 616-623
54. CrysAlis PRO version 171.34.49; Agilent Technologies, 2010.
55. Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220-229
56. Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33-38
57. SHELX: Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
58. PLATON: Spek, A. L. Acta Crystallogr. 2009, D65, 148-155