Fast CO2 sequestration, activation, and catalytic transformation using N -heterocyclic olefins

Journal of the American Chemical Society

Volumn 135, Issue 32, 2013, Pages 11996-12003

  Wang, Yan Bo ^a   Wang, Yi Ming ^a   Zhang, Wen Zhen ^a   Lu, Xiao Bing ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC TRANSFORMATION; CYCLIC CARBONATES; DEUTERIUM LABELING; PROPARGYLIC ALCOHOLS; RATE-LIMITING STEPS; SUBSTITUTE GROUPS; TERMINAL CARBON ATOMS; X-RAY SINGLE-CRYSTAL ANALYSIS;

ALCOHOLS; CARBONATES; CARBOXYLATION; CHEMICAL BONDS; ELECTRONEGATIVITY; OLEFINS;

CARBON DIOXIDE;

ALCOHOL DERIVATIVE; ALKENE; CARBON DIOXIDE; DEUTERIUM; N HETEROCYCLIC OLEFIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CYCLIZATION; DECARBOXYLATION; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; NUCLEOPHILICITY; ROOM TEMPERATURE;

EID: 84882279323     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405114e     Document Type: Article

References (97)

1. Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155-174
2. Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857-3898
3. Sakakura, T.; Choi, J. C.; Yasuda, H. Chem. Rev. 2007, 107, 2365-2386
4. Carbon Dioxide as Chemical Feedstock; Aresta, M., Ed.; Wiley-VCH: Weinheim, 2010.
5. Darensbourg, D. J. Inorg. Chem. 2010, 49, 10765-10780
6. Federsel, C.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 6254-6257
7. Huang, K.; Sun, C. L.; Shi, Z. J. Chem. Soc. Rev. 2011, 40, 2435-2452
8. Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510-8537
9. Omae, I. Coord. Chem. Rev. 2012, 256, 1384-1405
10. Lu, X.-B.; Darensbourg, D. J. Chem. Soc. Rev. 2012, 41, 1462-1484
11. Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259-272
12. Jessop, P. G.; Joo, F.; Tai, C.-C. Coord. Chem. Rev. 2004, 248, 2425-2442
13. Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196-17197
14. Ménard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796-1797
15. Ménard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2011, 50, 8396-8399
16. Bontemps, S.; Vendier, L.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2012, 51, 1671-1674
17. Sgro, M. J.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 11343-11345
18. Dobrovetsky, R.; Stephan, D. W. Angew. Chem., Int. Ed. 2013, 52, 2516-2519
19. Ménard, G.; Stephan, D. W. Dalton. Trans. 2013, 42, 5447-5453
20. Li, Y.; Fang, X.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52 10.1002/anie.2013 01349
21. Aresta, M.; Nobile, C. F. J. Chem. Soc. Chem. Commun. 1975, 636-637
22. Aresta, M.; Nobile, C. F. J. Chem. Soc. Dalton. Trans. 1977, 709-711
23. Gambarotta, S.; Arena, F.; Floriani, C.; Zanazzi, P. F. J. Am. Chem. Soc. 1982, 104, 5082-5092
24. Calabrese, J. C.; Herskovitz, T.; Kinney, J. B. J. Am. Chem. Soc. 1983, 105, 5914-5915
25. Pérez, E. R.; da Silva, M. O.; Costa, V. C.; Rodrigues-Filho, U. P.; Franco, D. W. Tetrahedron Lett. 2002, 43, 4091-4093
26. Barbarini, A.; Maggi, R.; Mazzacani, A.; Mori, G.; Sartori, G.; Sartorio, R. Tetrahedron Lett. 2003, 44, 2931-2934
27. Pérez, E. R.; Santos, R. H. A.; Gambardella, M. T. P. L.; de Macedo, G. M. U.; Rodrigues-Filho, P.; Launay, J. C.; Franco, D. W. J. Org. Chem. 2004, 69, 8005-8011
28. Heldebrant, D. J.; Jessop, P. G.; Thomas, C. A.; Eckert, C. A.; Thomas, C. A.; Eckert, C. A.; Liotta, C. L. J. Org. Chem. 2005, 70, 5335-5338
29. Pereira, F. S.; deAzevedo, E. R.; da Silva, E. F.; Bonagamba, T. J.; da Silva Agostíni, D. L.; Magalhães, A.; Job, A. E.; Pérez González, E. R. Tetrahedron. 2008, 64, 10097-10106
30. Villiers, C.; Dognon, J. P.; Pollet, R.; Thuéry, P.; Ephritikhine, M. Angew. Chem., Int. Ed. 2010, 49, 3465-3468
31. Holbrey, J. D.; Reichert, W. M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi, I.; Rogers, R. D. Chem. Commun. 2003, 28-29
32. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Chem. Commun. 2004, 112-113
33. Tudose, A.; Demonceau, A.; Delaude, L. J. Organomet. Chem. 2006, 691, 5356-5365
34. Voutchkova, A. M.; Feliz, M.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2007, 129, 12834-12846
35. Delaude, L. Eur. J. Inorg. Chem. 2009, 1681-1699
36. Van Ausdall, B. R.; Glass, J. L.; Wiggins, K. M.; Aarif, A. M.; Louie, J. J. Org. Chem. 2009, 74, 7935-7942
37. Zhou, H.; Zhang, W.-Z.; Liu, C.-H.; Qu, J.-P.; Lu, X.-B. J. Org. Chem. 2008, 73, 8039-8044
38. Riduan, S. N.; Zhang, Y.; Ying, J. -Y. Angew. Chem., Int. Ed. 2009, 48, 3322-3325
39. Gu, L.; Zhang, Y. J. Am. Chem. Soc. 2010, 132, 914-915
40. Nair, V.; Varghese, V.; Paul, R. R.; Jose, A.; Sinu, C. R.; Menon, R. S. Org. Lett. 2010, 12, 2653-2655
41. Huang, F.; Lu, G.; Zhao, L.; Li, H.; Wang, Z.-X. J. Am. Chem. Soc. 2010, 132, 12388-12396
42. Wang, C.-M; Luo, H.-M.; Jiang, D.; Li, H.-R.; Dai, S. Angew. Chem., Int. Ed. 2010, 49, 5978-5981
43. Wang, C.-M.; Luo, X.-Y.; Luo, H.-M.; Jiang, D.; Li, H.-R.; Dai, S. Angew. Chem., Int. Ed. 2011, 50, 4918-4922
44. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science. 2006, 314, 1124-1126
45. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535-1539
46. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
47. Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643-6646
48. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 13559-13568
49. Zhao, X.; Stephan, D. W. Chem. Commun. 2011, 47, 1833-1835
50. Sgro, M. J.; Dömer, J.; Stephan, D. W. Chem. Commun. 2012, 48, 7253-7255
51. Hounjet, L. J.; Caputo, C. B.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 4714-4717
52. Kantlehner, W. In Science of Synthesis; de Meijere, A., Ed.; Thieme: Stuttgart, 2006; Vol. 24; pp 571-705.
53. Keller, P. A.; Morgan, J. In Science of Synthesis; de Meijere, A., Ed.; Thieme: Stuttgart, 2006; Vol. 24; pp 707-746.
54. Ponti, P. P.; Baldwin, J. C.; Kaska, W. C. Inorg. Chem. 1979, 18, 873-875
55. Kuhn, N.; Bohnen, H.; Kreutzberg, J.; Bläser, D.; Boese, R. J. Chem. Soc. Chem. Commun. 1993, 1136-1137
56. Kuhn, N.; Bohnen, H.; Bläser, D.; Boese, R. Chem. Ber. 1994, 127, 1405-1407
57. Schuhmann, H.; Glanz, M.; Winterfeld, J.; Hemling, H.; Kuhn, N.; Bohnen, H.; BlMser, D.; Boese, R. J. Organomet. Chem. 1995, 493, C14-C18
58. Nakayama, J.; Akimoto, K.; Sugihara, Y. Tetrahedron Lett. 1998, 39, 5587-5590
59. Nakayama, J.; Kitahara, T.; Sugihara, Y.; Otani, T.; Ishii, A. Chem. Lett. 1998, 887-888
60. Rigby, J. H.; Lee, C.-S. Org. Lett. 2003, 5, 1151-1153
61. Fürstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 3210-3214
62. Glöckner, A.; Kronig, S.; Bannenberg, T.; Daniliuc, C. G.; Jones, P. G.; Tamm, M. J. Organomet. Chem. 2013, 723, 181-187
63. Al-Rafia, S. M. I.; Malcolm, A. C.; Liew, S. K.; Ferguson, M. J.; McDonald, R.; Rivard, E. Chem. Commun. 2011, 47, 6987-6989
64. Maji, B.; Horn, M.; Mayr, H. Angew. Chem., Int. Ed. 2012, 51, 6231-6235
65. Kronig, S.; Jones, P, G.; Tamm, M. Eur. J. Inorg. Chem. 2013, 2301-2314
66. Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792-5795
67. Boogaerts, I. I. F.; Nolan, S. P. J. Am. Chem. Soc. 2010, 132, 8858-8859
68. Yu, D.; Zhang, Y. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20184-20189
69. 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
70. Zhang, W.-Z.; Li, W.-J.; Zhang, X.; Zhou, H.; Lu, X.-B. Org. Lett. 2010, 12, 4748-4751
71. Ohishi, T.; Zhang, L.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2011, 50, 8114-8117
72. Zhang, X.; Zhang, W.-Z.; Ren, X.; Zhang, L.-L.; Lu, X.-B. Org. Lett. 2011, 13, 2402-2405
73. Li, S.; Yuan, W.; Ma, S. Angew. Chem., Int. Ed. 2011, 123, 2626-2630
74. Boogaerts, I. I. F.; Nolan, S. P. Chem. Commun. 2011, 47, 3021-3024
75. Zhang, X.; Zhang, W.-Z.; Shi, L.-L.; Guo, C.-X.; Zhang, L.-L.; Lu, X.-B. Chem. Commun. 2012, 48, 6292-6294
76. Toullec, P.; Martin, A. C.; Gio-Batta, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 2000, 41, 5527-5531
77. Ochiai, B.; Endo, T. Prog. Polym. Sci. 2005, 30, 183-215
78. Sasaki, Y. Tetrahedron Lett. 1986, 27, 1573-1574
79. Inoue, Y.; Ishikawa, J.; Taniguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1204-1206
80. Laas, H.; Nissen, A.; Nürrenbach, A. Synthesis 1981, 958-959
81. Kim, H.-S.; Kim, J.-W.; Kwon, S.-C.; Shim, S.-C.; Kim, T.-J. J. Organomet. Chem. 1997, 545-546, 337-344
82. Kwon, S.-C.; Cho, C.-S.; Shim, S.-C.; Kim, T.-J. Bull. Korean Chem. Soc. 1999, 20, 103-105
83. Gu, Y.; Shi, F.; Deng, Y. J. Org. Chem. 2004, 69, 391-394
84. Jiang, H.-F.; Wang, A.-Z.; Liu, H. -L.; Qi, C.-R. Eur. J. Org. Chem. 2008, 13, 2309-2312
85. Iritani, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1986, 51, 5499-5501
86. Uemura, K.; Kawaguchi, T.; Takayama, H.; Nakamura, A.; Inoue, Y. J. Mol. Catal. A: Chem. 1999, 139, 1-9
87. Yamada, W.; Sugawara, Y.; Cheng, H. M.; Ikeno, T.; Yamada, T. Eur. J. Org. Chem. 2007, 2007, 2604-2607
88. Sugawara, Y.; Yamada, W.; Yoshida, S.; Ikeno, T.; Yamada, T. J. Am. Chem. Soc. 2007, 129, 12902-12903
89. Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072-4073
90. Fournier, J.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 1989, 30, 3981-3982
91. Joumier, J. M.; Fournier, J.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc. Perkin Trans. 1. 1991, 3271-3274
92. Joumier, J. M.; Bruneau, C.; Dixneuf, P. H. Synlett. 1992, 453-454
93. Kayaki, Y.; Yamamoto, M.; Ikariya, T. J. Org. Chem. 2007, 72, 647-649
94. Della Ca', N.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133-146
95. Tommasi, I.; Sorrentino, F. Tetrahedron Lett. 2009, 50, 104-107
96. Kayaki, Y.; Yamamoto, M.; Ikariya, T. Angew. Chem., Int. Ed. 2009, 48, 4194-4197
97. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066-3072