Copper-catalyzed direct carboxylation of C-H bonds with carbon dioxide

Angewandte Chemie - International Edition

Volumn 49, Issue 46, 2010, Pages 8670-8673

  Zhang, Liang ^a   Cheng, Jianhua ^a   Ohishi, Takeshi ^a   Hou, Zhaomin ^a  

^a RIKEN   (Japan)

Author keywords

C H activation; carbene ligands; carbon dioxide; carboxylation; copper catalysts

Indexed keywords

C-H ACTIVATION; C-H BOND; CARBENE LIGANDS; CARBOXYLIC ESTERS; COPPER CATALYSTS; COPPER COMPLEXES; ENVIRONMENTALLY BENIGN PROCESS; IMIDAZOL-2-YLIDENE;

ACTIVATION ANALYSIS; BIOACTIVITY; CARBON DIOXIDE; CARBOXYLATION; CATALYSTS; COPPER; COPPER COMPOUNDS; ESTERS; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

LIGANDS;

EID: 78149418162     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003995     Document Type: Article

References (74)

1. Reviews
2. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347 3357
3. T. Sakakura, J. C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365 2387
4. A. Behr, Angew. Chem. 1988, 100, 681 698
5. Angew. Chem. Int. Ed. Engl. 1988, 27, 661 678
6. D. J. Darensbourg, Chem. Rev. 2007, 107, 2388 2410
7. N. Eghbali, C. J. Li, Green Chem. 2007, 9, 213 215
8. J. Louie, Curr. Org. Chem. 2005, 9, 605 623
9. T. J. Marks, et al., Chem. Rev. 2001, 101, 953 996.
10. Selected reviews
11. A. Correa, R. Martín, Angew. Chem. 2009, 121, 6317 6320
12. Angew. Chem. Int. Ed. 2009, 48, 6201 6204
13. Z. Hou, T. Ohishi, in Comprehensive Organometallic Chemistry III, Vol.10 (Eds.:, R.H. Crabtree, D.M.P. Mingos, I. Ojima,), Elsevier, Oxford, 2007, pp. 537 555.
14. M. Shi, K. M. Nicholas, J. Am. Chem. Soc. 1997, 119, 5057 5058
15. K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706 8707
16. J. Takaya, S. Tadami, K. Ukai, N. Iwasawa, Org. Lett. 2008, 10, 2697 2700
17. T. Ohishi, M. Nishiura, Z. Hou, Angew. Chem. 2008, 120, 5876 5879
18. Angew. Chem. Int. Ed. 2008, 47, 5792 5795
19. L. Dang, Z. Lin, Organometallics 2010, 29, 917 927
20. H. Ochiai, M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 2681 2683
21. C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 7826 7827
22. K. Kobayashi, Y. Kondo, Org. Lett. 2009, 11, 2035 2037
23. R. Johansson, O. F. Wendt, Dalton Trans. 2007, 488 492
24. A. Correa, R. Martín, J. Am. Chem. Soc. 2009, 131, 15974 15975
25. S. Saito, S. Nakagawa, T. Koizumi, K. Hirayama, Y. Yamamoto, J. Org. Chem. 1999, 64, 3975 3978
26. M. Aoki, M. Kaneko, S. Izumi, K. Ukai, N. Iwasawa, Chem. Commun. 2004, 2568 2569
27. M. Takimoto, Y. Nakamura, K. Kimura, M. Mori, J. Am. Chem. Soc. 2004, 126, 5956 5957
28. J. Louie, J. E. Gibby, M. V. Farnworth, T. N. Tekavec, J. Am. Chem. Soc. 2002, 124, 15188 15189
29. J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2008, 130, 15254 15255
30. C. M. Williams, J. B. Johnson, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14936 14937.
31. During the preparation of this manuscript, a report on gold-catalyzed carboxylation of C-H bonds appeared. The use of the copper catalyst [Cu(IPr)Cl] was also briefly noted, see:, I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858 8859.
32. L. J. Goossen, N. Rodriguez, K. Goossen, Angew. Chem. 2008, 120, 3144 3164
33. Angew. Chem. Int. Ed. 2008, 47, 3100 3120
34. S. P. Bew, in Comprehensive Organic Functional Groups Transformation II, (Eds.:, A.R. Katritzky, R.J.K. Taylor,), Elsevier, Oxford, 2005, p. 19
35. J. S. Stover, J. Shi, W. Jin, P. K. Vogt, D. Boger, J. Am. Chem. Soc. 2009, 131, 3342 3348
36. Y. Yin, L. Lin, C. Ruiz, M. D. Cameron, J. Pocas, W. Grant, T. Schroeter, W. Chen, D. Duckett, S. Schuerer, P. LoGrasso, Y. Feng, Bioorg. Med. Chem. Lett. 2009, 19, 6686 6690
37. G. Meroni, P. Ciana, A. Maggi, E. Santaniello, Synlett 2009, 2682 2684.
38. Reviews
39. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174 238
40. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976 10011
41. Angew. Chem. Int. Ed. 2009, 48, 9792 9826
42. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074 1086
43. A. Armstrong, J. C. Collins, Angew. Chem. 2010, 122, 2332 2335
44. Angew. Chem. Int. Ed. 2010, 49, 2282 2285
45. A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2010, 122, 2140 2142
46. Angew. Chem. Int. Ed. 2010, 49, 2096 2098, and references therein.
47. Selected examples
48. F. Besselievre, S. Piguel, F. Mahuteau-Betzer, D. S. Grierson, Org. Lett. 2008, 10, 4029 4032
49. R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172 8174
50. H. Q. Do, R. M. K. Khan, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 15185 15192
51. D. Zhao, W. Wang, F. Yang, J. Lan, L. Yang, G. Gao, J. You, Angew. Chem. 2009, 121, 3346 3350
52. Angew. Chem. Int. Ed. 2009, 48, 3296 3300
53. H. Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404 12405
54. T. Yoshizumi, H, Tsurugi, T. Satoh, M. Miura, Tetrahedron Lett. 2008, 49, 1598 1600
55. I. Ban, T. Sudo, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 3607 3609
56. L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett. 2008, 10, 3081 3084
57. L. Yang, Z. Lu, S. S. Stahl, Chem. Commun. 2009, 6460 6462
58. X. Chen, X. S. Hao, C. E. Goodhue, J. Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790 6791
59. D. Monguchi, T. Fujiwara, H. Furukawa, A. Mori, Org. Lett. 2009, 11, 1607 1610
60. Q. Wang, S. L. Schreiber, Org. Lett. 2009, 11, 5178 5180
61. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900 6901
62. T. Kawano, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2010, 75, 1764 1766
63. F. Besselièvre, S. Piguel, Angew. Chem. 2009, 121, 9717 9720
64. Angew. Chem. Int. Ed. 2009, 48, 9553 9556
65. H. Zhao, M. Wang, W. Su, M. Hong, Adv. Synth. Catal. 2010, 352, 1301 1306.
66. S. Diez-González, S. P. Nolan, Synlett 2007, 2158 2167
67. V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 2003, 5, 2417 2420
68. H. Kaur, F. K. Zinn, E. D. Stevens, S. P. Nolan, Organometallics 2004, 23, 1157 1160
69. D. S. Laitar, P. Muller, J. P. Sadighi, J. Am. Chem. Soc. 2005, 127, 17196 17197
70. T. G. David, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 1191 1193.
71. The decomposition of benzoxazole-2-carboxylic acid under acidic conditions was also observed previously., D. L. Boger, B. E. Fink, M. P. Hedrick, J. Am. Chem. Soc. 2000, 122, 6382 6394.
72. K. Shen, Y. Fu, J. N. Li, L. Liu, Q. X. Guo, Tetrahedron 2007, 63, 1568 1576.
73. N. P. Mankad, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 3369 3371.
74. CCDC782839 (3) and CCDC782840 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.