A unique copper-catalyzed cross-coupling reaction by hydrogen (H2) removal for the stereoselective synthesis of 3-phosphoindoles

Chemical Communications

Volumn 50, Issue 62, 2014, Pages 8529-8532

  Zhou, An Xi ^a   Mao, Liu Liang ^a   Wang, Gang Wei ^a   Yang, Shang Dong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHOSPHOINDOLE; COPPER; FOSDEVIRINE; HYDROGEN; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CLINICAL TRIAL (TOPIC); CROSS COUPLING REACTION; DEHYDROGENATION; HYDROGEN BOND; PHOSPHORYLATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 84904089144     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01815j     Document Type: Article

References (50)

1. D. Dyker, Handbook of C-H Transformation, Wiley-VCH, Weinheim, 2005, vol. 1.
2. J.-Q. Yu and Z.-J. Shi, C-H Activation, Springer-Verlag, Berlin Heidelberg, 2010.
3. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173.
4. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094.
5. W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev. 2011, 40, 1976.
6. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 10236.
7. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215.
8. J. L. Bras, J. Muzart, Chem. Rev. 2011, 111, 1170.
9. C. J. Scheuermann, Chem. - Asian J. 2010, 5, 436.
10. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74.
11. T. Stahl, K. Müther, Y. Ohki, K. Tatsumi, M. Oestreich, J. Am. Chem. Soc. 2013, 135, 10978.
12. Q. Meng, J. Zhong, Q. Liu, X. Gao, H. Zhang, T. Lei, Z. Li, K. Feng, B. Chen, C. Tung, L. Wu, J. Am. Chem. Soc. 2013, 135, 19052.
13. B. A. Atta-ur-Rahman, Indole Alkaloids, Harwood Academic, Chichester, 1998.
14. F.-E. Chen, J. Huang, Chem. Rev. 2005, 105, 4671.
15. B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050.
16. N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972.
17. R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172.
18. S. J. Hwang, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2008, 130, 16158.
19. N. Lebrasseur, I. Larrosa, J. Am. Chem. Soc. 2008, 130, 2926.
20. S.-D. Yang, C.-L. Sun, Z. Fang, B.-J. Li, Y.-Z. Li, Z.-J. Shi, Angew. Chem. Int. Ed. 2008, 47, 1473.
21. S. Ding, Z. Shi, N. Jiao, Org. Lett. 2010, 12, 1540.
22. S. Ding, N. Jiao, J. Am. Chem. Soc. 2011, 133, 12374.
23. Q. Liu, G. Li, H. Yi, P. Wu, J. Liu, A. Lei, Chem. - Eur. J. 2011, 17, 2353.
24. S. Pan, N. Ryu, T. Shibata, J. Am. Chem. Soc. 2012, 134, 17474.
25. L. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc. 2012, 134, 14563.
26. T. Stahl, K. Müther, Y. Ohki, K. Tatsumi, M. Oestreich, J. Am. Chem. Soc. 2013, 135, 10978.
27. Y.-M. Li, M. Sun, H.-L. Wang, Q.-P. Tian, S.-D. Yang, Angew. Chem. Int. Ed. 2013, 52, 3972.
28. Y.-M. Li, S.-D. Yang, Synlett, 2013, 1739.
29. H.-Y. Zhang, M. Sun, Y. N. Ma, Q. P. Tian, S. D. Yang, Org. Biomol. Chem. 2012, 10, 9627.
30. J. Hu, N. Zhao, B. Yang, G. Wang, L. N. Guo, Y. M. Liang, S. D. Yang, Chem. - Eur. J. 2011, 17, 5516.
31. M. Sun, H. Y. Zhang, Q. Han, K. Yang, S. D. Yang, Chem. - Eur. J. 2011, 17, 9566.
32. X. J. Zhou, R. C. Garner, S. Nicholson, C. J. Kissling, D. Mayers, J. Clin. Pharmacol. 2009, 49, 1408.
33. F. R. Alexandre, A. Amador, S. Bot, C. Caillet, T. Convard, J. Jakubik, C. Musiu, B. Poddesu, L. Vargiu, M. Liuzzi, A. Roland, M. Seifer, D. Standring, R. Storer, C. B. Dousson, J. Med. Chem. 2011, 54, 392.
34. R. Storer, C. Dousson, F. R. Alexandre and A. Roland, Phosphoindoles as HIV inhibitors, WO PCT Int. Appl. 054182, 2006.
35. X.-J. Zhou, K. Pietropaolo, D. Damphousse, B. Belanger, J. Chen, J. Sullivan-Bólyai, D. Mayers, Antimicrob. Agents Chemother. 2009, 53, 1739.
36. G. La Regina, A. Coluccia, R. Silvestri, Antiviral Chem. Chemother. 2010, 20, 213.
37. O. Baslé, C.-J. Li, Chem. Commun. 2009, 4124.
38. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc. 2009, 131, 7956.
39. C.-B. Xiang, Y.-J. Bian, X.-R. Mao, Z.-Z. Huang, J. Org. Chem. 2012, 77, 7706.
40. C. Hou, Y. Ren, R. Lang, X. Hu, C. Xia, F. Li, Chem. Commun. 2012, 48, 5181.
41. C.-G. Feng, M. Ye, K.-J. Xiao, S. Li, J.-Q. Yu, J. Am. Chem. Soc. 2013, 135, 9322.
42. C. Li, T. Yano, N. Ishida, M. Murakami, Angew. Chem. Int. Ed. 2013, 52, 9801.
43. W. G. Bentrude, in The Chemistry of Organophosphorus Compounds, ed. F. R. Hartley, Wiley, New York, 1990, vol. 1, ch. 14.
44. O. Tayama, A. Nakano, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 5494.
45. W. Wei, J. X. Ji, Angew. Chem. Int. Ed. 2011, 50, 9097.
46. J. E. Baxter, R. S. D. Makromol, Makromol. Chem. Rapid Commun. 1987, 8, 311.
47. C. Deutsch, N. Krause, Chem. Rev. 2008, 108, 2916.
48. L.-B. Han, M. Tanaka, Chem. Commun. 1999, 395.
49. L.-B. Han, T. D. Tilley, J. Am. Chem. Soc. 2006, 128, 13698.
50. L.-B. Han, Y. Ono, S. Shimada, J. Am. Chem. Soc. 2008, 130, 2752.