NHC-Gold(I) complexes as effective catalysts for the carboxylative cyclization of propargylamines with carbon dioxide

Organometallics

Volumn 32, Issue 19, 2013, Pages 5285-5288

  Hase, Shun ^a   Kayaki, Yoshihito ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATIONIC GOLD; CYCLIC URETHANES; MIXED GAS; PROPARGYLAMINES; PROPARGYLIC AMINES; SITU GENERATION; SOLVENT INFLUENCE; STOICHIOMETRIC REACTION;

CARBON DIOXIDE; CATALYSTS; CYCLIZATION; GOLD; METHANOL; ORGANIC SOLVENTS; REACTION INTERMEDIATES;

GOLD COMPOUNDS;

EID: 84885615050     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400949m     Document Type: Article

References (62)

1. Omae, I. Coord. Chem. Rev. 2012, 256, 1384-1405
2. Darensbourg, D. J. Inorg. Chem. 2010, 49, 10765-10780
3. Boddien, A.; Gärtner, F.; Federsel, C.; Piras, I.; Junge, H.; Jackstell, R.; Beller, M. In Organic Chemistry-Breakthroughs and Perspectives; Ding, K.; Dai, L.-X., Eds.; Wiley-VCH: Weinheim, Germany, 2012; pp 685-722.
4. Yang, Z.-Z.; He, L. N.; Gao, J.; Liu, A.-H.; Yu, B. Energy Environ. Sci. 2012, 5, 6602-6639
5. Chaturvedi, D.; Chaturvedi, A. K.; Mishra, V. Curr. Org. Chem. 2012, 16, 1609-1635
6. Quaranta, E.; Aresta, M. In Carbon Dioxide as Chemical Feedstock; Aresta, M., Ed.; Wiley-VCH: Weinheim, Germany, 2010; pp 121-167.
7. Kayaki, Y.; Yamamoto, M.; Suzuki, T.; Ikariya, T. Green Chem. 2006, 8, 1019-1021
8. Kayaki, Y.; Suzuki, T.; Ikariya, T. Chem. Asian J. 2008, 3, 1865-1870
9. Kayaki, Y.; Suzuki, T.; Noguchi, Y.; Sakurai, S.; Imanari, M.; Ikariya, T. Chem. Lett. 2002, 31, 424-425
10. Kayaki, Y.; Mori, N.; Ikariya, T. Tetrahedron Lett. 2009, 50, 6491-6493
11. Ihata, O.; Kayaki, Y.; Ikariya, T. Angew. Chem., Int. Ed. 2004, 43, 717-719
12. Ihata, O.; Kayaki, Y.; Ikariya, T. Macromolecules 2005, 38, 6429-6434
13. Ihata, O.; Kayaki, Y.; Ikariya, T. Chem. Commun. 2005, 41, 2268-2270
14. Seki, T.; Kokubo, Y.; Ichikawa, S.; Suzuki, T.; Kayaki, Y.; Ikariya, T. Chem. Commun. 2009, 45, 349-351
15. Dimroth, P.; Pasedach, H. DE Pat 1164411, 1964
16. Chem. Abstr. 1964, 60, 14510.
17. Mitsudo, T.; Hori, Y.; Yamakawa, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 4417-4418
18. Costa, M.; Chiusoli, G. P.; Rizzardi, M. J. Chem. Soc., Chem. Commun. 1996, 1699-1700
19. Costa, M.; Chiusoli, G. P.; Taffurelli, D.; Dalmonego, G. J. Chem. Soc., Perkin Trans. 1 1998, 1541-1546
20. Shi, M.; Shen, Y.-M. J. Org. Chem. 2002, 67, 16-21
21. Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. Chem. Lett. 2009, 38, 786-787
22. Kikuchi, S.; Yoshida, S.; Sugawara, Y.; Yamada, W.; Cheng, H.-M.; Fukui, K.; Sekine, K.; Iwakura, I.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2011, 84, 698-717
23. Ishida, T.; Kikuchi, S.; Tsubo, T.; Yamada, T. Org. Lett. 2013, 15, 848-851
24. Modern Gold Catalyzed Synthesis; Hashmi, A. S. K.; Toste, F. D., Eds.; Wiley-VCH: Weinheim, Germany, 2012.
25. Ito, S.; Kusano, S.; Morita, N.; Mikami, K.; Yoshifuji, M. J. Organomet. Chem. 2010, 695, 291-296
26. Harkat, H.; Dembelé, A. Y.; Weibel, J.-M.; Blanc, A.; Pale, P. Tetrahedron 2009, 65, 1871-1879
27. Harkat, H.; Weibel, J.-M.; Pale, P. Tetrahedron Lett. 2006, 47, 6273-6276
28. Marchal, E.; Uriac, P.; Legouin, B.; Toupet, L.; van de Weghe, P. Tetrahedron 2007, 63, 9979-9990
29. Utilization of NHC-Au(I) catalysts in carboxylation: Boogaerts, I. I. F.; Nolan, S. P. J. Am. Chem. Soc. 2010, 132, 8858-8859
30. Shintani, R.; Nozaki, K. Organometallics 2013, 32, 2459-2462
31. Zhang, L.; Cheng, J.; Hou, Z. Chem. Commun. 2013, 49, 4782-4784
32. Zhang, L.; Cheng, J.; Carry, B.; Hou, Z. J. Am. Chem. Soc. 2012, 134, 14314-14317
33. Fujihara, T.; Tani, Y.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2012, 51, 11487-11490
34. Inomata, H.; Ogata, K.; Fukuzawa, S.-i.; Hou, Z. Org. Lett. 2012, 14, 3986-3989
35. Kleeberg, C.; Cheung, M. S.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2011, 133, 19060-19063
36. Ohishi, T.; Zhang, L.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2011, 50, 8114-8117
37. Fujihara, T.; Xu, T.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2011, 50, 523-527
38. Yu, D.; Zhang, Y. Proc. Natl. Acad. Sci. U.S.A 2010, 107, 20184-20189
39. Zhang, W.-Z.; Li, W.-J.; Zhang, X.; Zhou, H.; Lu, X.-B. Org. Lett. 2010, 12, 4748-4751
40. Zhang, L.; Cheng, J.; Ohishi, T.; Hou, Z. Angew. Chem., Int. Ed. 2010, 49, 8670-8673
41. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem., Int. Ed. 2010, 49, 8674-8677
42. Kayaki, Y.; Yamamoto, M.; Ikariya, T. Angew. Chem., Int. Ed. 2009, 48, 4194-4197
43. Ueno, A.; Kayaki, Y.; Ikariya, T. Green Chem. 2013, 15, 425-430
44. Gómez-Suárez, A.; Ramón, R. S.; Slawin, A. M. Z.; Nolan, S. P. Dalton Trans. 2012, 41, 5461-5463
45. Liu, L.-P.; Hammond, G. B. Chem. Soc. Rev. 2012, 41, 3129-3139
46. Liu, L.-P.; Xu, B.; Mashuta, M. S.; Hammond, G. B. J. Am. Chem. Soc. 2008, 130, 17642-17643
47. Hashmi, A. S. K.; Schuster, A. M.; Rominger, F. Angew. Chem., Int. Ed. 2009, 48, 8247-8249
48. Hashmi, A. S. K.; Ramamurthi, T. D.; Rominger, F. Adv. Synth. Catal. 2010, 352, 971-975
49. Döpp, R.; Lothschütz, C.; Wurn, T.; Pernpointner, M.; Keller, S.; Rominger, F.; Hashmi, A. S. K. Organometallics 2011, 30, 5894-5903
50. Hashmi, A. S. K.; Schuster, A. M.; Gaillard, S.; Cavallo, L.; Poater, A.; Nolan, S. P. Organometallics 2011, 30, 6328-6337
51. Hashmi, A. S. K.; Braun, I.; Nösel, P.; Schädlich, J.; Wieteck, M.; Rudolph, M.; Rominger, F. Angew. Chem., Int. Ed. 2012, 51, 4456-4460
52. Weber, D.; Tarselli, M. A.; Gagné, M. R. Angew. Chem., Int. Ed. 2009, 48, 5733-5736
53. Shi, Y.; Ramgren, S. D.; Blum, S. A. Organometallics 2009, 28, 1275-1277
54. Cornell, T. P.; Shi, Y.; Blum, S. A. Organometallics 2012, 31, 5990-5993
55. Zeng, X.; Kinjo, R.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49, 942-945
56. Chen, Y.; Wang, D.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. Chem. Commun. 2010, 46, 6147-6149
57. Zhu, Y.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 8329-8332
58. Egorova, O. A.; Seo, H.; Kim, Y.; Moon, D.; Rhee, Y. M.; Ahn, K. H. Angew. Chem., Int. Ed. 2011, 50, 11446-11450
59. Joost, M.; Gualco, P.; Mallet-Ladeira, S.; Amgoune, A.; Bourissou, D. Angew. Chem., Int. Ed. 2013, 52, 7160-7163
60. Gattow, G.; Behredt, W. Angew. Chem., Int. Ed. 1972, 11, 534-535
61. Dibenedetto, A.; Aresta, M.; Giannoccaro, P.; Pastore, C.; Pápai, I.; Schubert, G. Eur. J. Inorg. Chem. 2006, 908-913
62. Gohres, J. L.; Marin, A. T.; Lu, J.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 2009, 48, 1302-1306