Silver-promoted oxidative cyclization of 1,6-enynes: Highly regioselective synthesis of phosphorated fluorene derivatives

Organic Letters

Volumn 16, Issue 21, 2014, Pages 5616-5619

  Zhou, Zhao Zhao ^a   Jin, Dong Po ^a   Li, Lian Hua ^a   He, Yu Tao ^a   Zhou, Ping Xin ^a   Yan, Xiao Biao ^a   Liu, Xue Yuan ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; FLUORENE; FLUORENE DERIVATIVE; PHOSPHINE DERIVATIVE; SILVER;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; FLUORENES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOSPHINES; SILVER; STEREOISOMERISM;

EID: 84909989461     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502397f     Document Type: Article

References (54)

1. Quin, L. D. A Guide to Organophosphorus Chemistry; John Wiley & Sons: 2000.
2. Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858
3. Albrecht, A.; Albrecht, A.; Krawczyk, H.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 28
4. Zhao, D.; Wang, R. Chem. Soc. Rev. 2012, 41, 2095
5. Bialy, L.; Waldmann, H. Angew. Chem., Int. Ed. 2005, 44, 3814
6. George, A.; Veis, A. Chem. Rev. 2008, 108, 4670
7. Bezombes, J.-P.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Mater. Chem. 1998, 8, 1749
8. Wang, G.-W.; Wang, C.-Z.; Zou, J.-P. J. Org. Chem. 2011, 76, 6088
9. Benin, V.; Durganala, S.; Morgan, A. B. J. Mater. Chem. 2012, 22, 1180
10. Xiang, D.; Huang, P.; Wang, K.; Zhou, G.; Liang, Y.; Dong, D. Chem. Commun. 2008, 6236
11. Amareshwar, V.; Mishra, N. C.; Ila, H. Org. Biomol. Chem. 2011, 9, 5793
12. Xu, Q.; Zhao, C.-Q.; Han, L.-B. J. Am. Chem. Soc. 2008, 130, 12648
13. Brands, K. M. J.; Jobson, R. B.; Conrad, K. M.; Williams, J. M.; Pipik, B.; Cameron, M.; Davies, A. J.; Houghton, P. G.; Ashwood, M. S.; Cottrell, F.; Reamer, R. A.; Kennedy, D. J.; Dolling, U.; Reider, P. J. J. Org. Chem. 2002, 67, 4771
14. Slowinski, F.; Aubert, C.; Malacria, M. J. Org. Chem. 2003, 68, 378
15. Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315
16. Xu, Q.; Han, L.-B. Org. Lett. 2006, 8, 2099
17. Alnasleh, B. K.; Sherrill, W. M.; Rubin, M. Org. Lett. 2008, 10, 3231
18. Kale, M.; Ziadi, A.; Stawinski, J. Org. Lett. 2008, 10, 4637
19. Zhang, X.; Liu, H.; Hu, X.; Tang, G.; Zhu, J.; Zhao, Y. Org. Lett. 2011, 13, 3478
20. Feng, C.-G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 9322
21. Beaufils, F.; Denes, F.; Renaud, P. Angew. Chem., Int. Ed. 2005, 44, 5273
22. Han, L.-B.; Zhao, C.-Q. J. Org. Chem. 2005, 70, 10121
23. Pan, X.-Q.; Zou, J.-P.; Zhang, G.-L.; Zhang, W. Chem. Commun. 2010, 46, 1721
24. Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875
25. Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14082
26. Chu, X.-Q.; Zi, Y.; Meng, H.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2014, 50, 7642
27. Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095
28. Li, D.-P.; Pan, X.-Q.; An, L.-T.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2014, 79, 1850
29. Zhou, M.-B.; Song, R.-J.; Ouyang, X.-H.; Liu, Y.; Wei, W.-T.; Deng, G.-B.; Li, J.-H. Chem. Sci. 2013, 4, 2690
30. Fan, J.-H.; Wei, W.-T.; Zhou, M.-B.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2014, 53, 6650
31. Zhou, Z.-Z.; Hua, H.-L.; Luo, J.-Y.; Chen, Z.-S.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Tetrahedron 2013, 69, 10030
32. Meng, Y.; Guo, L.-N.; Wang, H.; Duan, X.-H. Chem. Commun. 2013, 49, 7540
33. Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972
34. Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875
35. Li, D.-P.; Pan, X.-Q.; An, L.-T.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2014, 79, 1850
36. Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356
37. Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250
38. Chen, Y.-R.; Duan, W.-L. J. Am. Chem. Soc. 2013, 135, 16754
39. Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 12975
40. Deng, G.-B.; Wang, Z.-Q.; Xia, J.-D.; Qian, P.-C.; Song, R.-J.; Hu, M.; Gong, L.-B.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 1535
41. Liu, Y.; Zhang, J.-L.; Song, R.-J.; Qian, P.-C.; Li, J.-H. Angew. Chem., Int. Ed. 2014, 53, 9017
42. Morgan, L. R.; Thangaraj, K.; LeBlanc, B.; Rodgers, A.; Wolford, L. T.; Hooper, C. L.; Fan, D.; Jursic, B. S. J. Med. Chem. 2003, 46, 4552
43. Yue, Q.; Jiang, X.; De, R. Org. Lett. 2007, 9, 4371
44. Yeh, H.-C.; Chien, C.-H.; Shih, P.; Yuan, M.-C.; Shu, C.-F. Macromolecules 2008, 41, 3801
45. Saikawa, Y.; Hashimoto, K.; Nakata, M.; Yoshihara, M.; Nagai, K.; Ida, M.; Komiya, T. Nature 2004, 429, 363
46. Leca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858
47. Geoffroy, M.; Lucken, E. A. C. Mol. Phys. 1971, 22, 257
48. Kerr, C. M. L.; Webster, K.; Williams, F. J. Phys. Chem. 1975, 79, 2650
49. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029
50. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
51. Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727
52. Li, Y.; Lu, L.-Q.; Das, S.; Pisiewicz, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 18325
53. Gao, P.; Yan, X.-B.; Tao, T.; Yang, F.; He, T.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2013, 19, 14420
54. He, Y.-T.; Li, L.-H.; Zhou, Z.-Z.; Hua, H.-L.; Qiu, Y.-F.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 3896