Manganese(III)-mediated selective diphenylphosphinoyl radical reaction of 1,4-diaryl-1-butynes for the synthesis of 2-phosphinoylated 3,4- dihydronaphathalenes

Journal of Organic Chemistry

Volumn 79, Issue 4, 2014, Pages 1850-1855

  Li, Da Peng ^a   Pan, Xiang Qiang ^a   An, Li Tao ^d   Zou, Jian Ping ^a,b   Zhang, Wei ^c  

^a SOOCHOW UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

^d HUAIYIN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894558473     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402556a     Document Type: Article

References (33)

1. Laca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858
2. Marque, S.; Tordo, P. Top. Curr. Chem. 2005, 250, 43
3. Deprele, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745
4. Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Tetrahedron: Asymmetry 2003, 14, 2849
5. Beaufils, F.; Denes, F.; Renaud, P. Angew. Chem., Int. Ed. 2005, 44, 5273
6. Brumwell, J. E.; Simpkins, N. S.; Terrett, N. K. Tetrahedron 1994, 50, 13533
7. Lamarque, C.; Beaufils, F.; Denes, F.; Schenk, K.; Renaud, P. Adv. Synth. Catal. 2011, 353, 1353
8. Herpin, T. F.; Motherwell, W. B.; Roberts, B. P.; Roland, S.; Weibel, J.-M. Tetrahedron 1997, 53, 15085
9. Rey, P.; Taillades, J.; Rossi, J. C.; Gros, G. Tetrahedron Lett. 2003, 44, 6169
10. Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Tetrahedron Lett. 2003, 44, 479
11. Cho, D. H.; Jany, D. O. Synlett 2005, 59
12. Healy, M. P.; Parsons, A. F.; Rawlinson, J. G. T. Synlett 2008, 329
13. Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Eur. J. Org. Chem. 2006, 1547
14. Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137
15. Pan, X.-Q.; Zou, J.-P.; Wang, L.; Zhang, W. Chem. Commun. 2010, 46, 1721
16. Zhou, J.; Zhang, G.-L.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem. 2011, 3412
17. Zhou, P.; Jiang, Y.-J.; Zou, J.-P.; Zhang, W. Synthesis 2012, 44, 1043
18. Sun, W. B.; Ji, Y.-F.; Pan, X.-Q.; Zhou, S.-F.; Zou, J.-P.; Zhang, W.; Asekun, O. Synthesis 2013, 45, 1529
19. Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875
20. Xu, W.; Zou, J.-P.; Zhang, W. Tetrahedron Lett. 2010, 51, 2639
21. Santi, R.; Bergamini, F. J. Org. Chem. 1992, 57, 4250
22. de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Plenum Press: New York, 1986.
23. Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 2005, 46, 3755
24. Zhang, X. X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230
25. Egi, M.; Kawai, T.; Umemura, M.; Akai, S. J. Org. Chem. 2012, 77, 7092
26. Yasuhara, Y.; Nishimura, T.; Hayashi, T. Chem. Commun 2010, 12, 2130
27. Kwong, A. W.; Fu, M. Y.; Law, H. C.; Toy, P. H. Synlett 2010, 17, 2617
28. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148
29. Lingam, V. S.; Vinodkumar, R.; Mukkanti, K. Tetrahedron Lett. 2008, 49, 4260
30. Zhang, X. X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 5, 763
31. Dinges, J.; Albert, D. H.; Arnold, L. D. J. Med. Chem. 2007, 50, 2011
32. Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 7, 2719
33. Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. J. Org. Chem. 2007, 72, 5104