Brønsted acid enhanced rhodium-catalyzed conjugate addition of aryl C-H bonds to α,β-unsaturated ketones under mild conditions

Chemistry - A European Journal

Volumn 18, Issue 31, 2012, Pages 9511-9515

  Yang, Lei ^a   Qian, Bo ^a   Huang, Hanmin ^a,b  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

C H activation; conjugate addition; ketones; proton transfer; rhodium

Indexed keywords

C-H ACTIVATION; C-H BOND; CONJUGATE ADDITION; MILD REACTION CONDITIONS; RHODIUM-CATALYZED; SUBSTRATE INHIBITION; UNSATURATED KETONES;

ACTIVATION ANALYSIS; ADDITION REACTIONS; CATALYSIS; KETONES; PROTON TRANSFER; RHODIUM;

ORGANIC COMPOUNDS;

EID: 84864153161     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201348     Document Type: Article

References (62)

1. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731
2. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077
3. X. Wang, L. Zhou, W. Lu, Curr. Org. Chem. 2010, 14, 289
4. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
5. Y. Kuninobu, Y. Nishina, C. Nakagawa, K. Takai, J. Am. Chem. Soc. 2006, 128, 12376
6. Y. Kuninobu, Y. Nishina, T. Takeuchi, K. Takai, Angew. Chem. 2007, 119, 6638
7. Angew. Chem. Int. Ed. 2007, 46, 6518
8. Y. Kuninobu, Y. Nishina, K. Takai, Tetrahedron 2007, 63, 8463
9. L. Yang, C. A. Correia, C.-J. Li, Adv. Synth. Catal. 2011, 353, 1269
10. B.-J. Li, Z.-J. Shi, Chem. Sci. 2011, 2, 488
11. Y. Li, X.-S. Zhang, K. Chen, K.-H. He, F. Pan, B.-J. Li, Z.-J. Shi, Org. Lett. 2012, 14, 636.
12. J. Aydin, K. J. Szabõ, Org. Lett. 2008, 10, 2881
13. J. Aydin, C. S. Conrad, K. J. Szabõ, Org. Lett. 2008, 10, 5175
14. B. Qian, S. Guo, J. Shao, Q. Zhu, L. Yang, C. Xia, H. Huang, J. Am. Chem. Soc. 2010, 132, 3650
15. A. S. Tsai, M. E. Tauchert, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 1248
16. Y. Li, W.-H. Wang, W.-P. Huang, X.-S. Zhang, K. Chen, Z.-J. Shi, Angew. Chem. 2011, 123, 2163
17. Angew. Chem. Int. Ed. 2011, 50, 2115
18. M. E. Tauchert, C. D. Incarvito, A. L. Rheingold, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2012, 134, 1482
19. Y. Li, X.- Zhang, H. Li, W.-H. Wang, K. Chen, B.-J. Li, Z.-J. Shi, Chem. Sci. 2012, 3, 1634.
20. Y. Kuninobu, K. Kikuchi, Y. Tokunaga, Y. Nishina, K. Takai, Tetrahedron 2008, 64, 5974
21. Y. Kuninobu, Y. Fujii, T. Matsuki, Y. Nishina, K. Takai, Org. Lett. 2009, 11, 2711
22. Z.-M. Sun, P. Zhao, Angew. Chem. 2009, 121, 6854
23. Angew. Chem. Int. Ed. 2009, 48, 6726
24. Z.-M. Sun, J. Zhang, R. S. Manan, P. Zhao, J. Am. Chem. Soc. 2010, 132, 6935
25. C. Zhao, F. D. Toste, R. G. Bergman, J. Am. Chem. Soc. 2011, 133, 10787.
26. Electron and Proton Transfer in Chemistry and Biology (Ed.:, A. Muller,) Elsevier, Amsterdam, 1992
27. D. A. Evans, M. C. Willis, J. N. Johnston, Org. Lett. 1999, 1, 865
28. J. Zhou, M.-C. Ye, Z.-Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309
29. J. Zhou, Y. Tang, Chem. Commun. 2004, 432
30. T. Arai, N. Yokoyama, Angew. Chem. 2008, 120, 5067
31. Angew. Chem. Int. Ed. 2008, 47, 4989
32. L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia, H. Huang, Chem. Eur. J. 2010, 16, 1638.
33. K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169
34. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829.
35. L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35
36. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222
37. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
38. C.-J. Li, Acc. Chem. Res. 2009, 42, 335
39. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
40. Angew. Chem. Int. Ed. 2009, 48, 5094
41. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. 2009, 121, 9976
42. Angew. Chem. Int. Ed. 2009, 48, 9792
43. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
44. K. Fagnou, Top. Curr. Chem. 2010, 292, 35
45. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
46. C. J. Scheuermann, Chem. Asian J. 2010, 5, 436
47. S.-L. You, J.-B. Xia, Top. Curr. Chem. 2010, 292, 165
48. L.-M. Xu, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712
49. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
50. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
51. W. Shi, C. Liu, A. Lei, Chem. Soc. Rev. 2011, 40, 2761
52. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
53. J. Wencel-Delord, T. Droge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740; For selected reviews on rhodium-catalyzed C-H activation, see
54. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
55. J. Bouffard, K. Itami, Top. Curr. Chem. 2010, 292, 231
56. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
57. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814
58. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651.
59. B. Qian, S. Guo, C. Xia, H. Huang, Adv. Synth. Catal. 2010, 352, 3195
60. S. Guo, B. Qian, Y. Xie, C. Xia, H. Huang, Org. Lett. 2011, 13, 522
61. B. Qian, P. Xie, Y. Xie, H. Huang, Org. Lett. 2011, 13, 2580.
62. When we were preparing this manuscript, Li and co-workers reported the direct addition of aryl C-H bonds to several aliphatic α,β- unsaturated ketones, trans-2-pentenal, and cinnaldehyde derivatives, but relatively harsh reaction conditions and longer reaction times (48-72 h) were needed., L. Yang, C. A. Correia, C.-J. Li, Org. Biomol. Chem. 2011, 9, 7176.