UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions

Organic Letters

Volumn 17, Issue 4, 2015, Pages 1034-1037

  Zheng, Lewei ^a   Huang, Hongli ^a   Yang, Chao ^a   Xia, Wujiong ^a  

^a HARBIN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84923348172     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00144     Document Type: Article

References (40)

1. Jacques, B. and Muiňz, K. In Catalyzed Carbon-Heteroatom Bond Formation; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2010; pp 119-135.
2. Sibbald, P. A. Palladium-catalyzed oxidative difunctionalization of alkenes: New reactivity and new mechanisms; ProQuest, UMI Dissertation Publishing: 2011.
3. Bergmeier, S. C. Tetrahedron 2000, 56, 2561
4. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
5. Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910
6. Li, G.; Kotti, S. R. S. S.; Timmons, C. Eur. J. Org. Chem. 2007, 72, 2745
7. Muňiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
8. Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009
9. Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083
10. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981
11. Zhang, C.; Tang, C.; Jia, N. Chem. Soc. Rev. 2012, 41, 3464
12. Wu, T.; Mu, X.; Liu, G.-S. Angew. Chem., Int. Ed. 2011, 50, 12578
13. Mu, X.; Wu, T.; Wang, H.-Y.; Guo, Y.-L.; Liu, G.-S. J. Am. Chem. Soc. 2012, 134, 878
14. Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638
15. Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972
16. Li, X.; Xu, X.; Hu, P.; Xiao, X.; Zhou, C. J. Org. Chem. 2013, 78, 7343
17. Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985
18. Meng, Y.; Guo, L.-N.; Wang, H.; Duan, X.-H. Chem. Commun. 2013, 49, 7540
19. 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
20. Wu, T.; Zhang, H.; Liu, G. Tetrahedron 2012, 68, 5229
21. Jia, F.; Liu, K.; Xi, H.; Lu, S.; Li, Z. Tetrahedron. Lett. 2013, 54, 6337
22. Wang, H.; Guo, L.-N.; Duan, X.-H. Adv. Synth. Catal. 2013, 355, 2222
23. Hoffmann, N. Chem. Rev. 2008, 108, 1052
24. Fleck, M.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 6189
25. Selig, P.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 5082
26. Veerman, M.; Resendiz, M. J.; Garcia-Garibay, M. A. Org. Lett. 2006, 8, 2615
27. Mortko, C. J.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2005, 12, 7994
28. Fagnoni, M.; Albini, A. Acc. Chem. Res. 2005, 38, 713
29. Roth, H. D. Angew. Chem., Int. Ed. 1989, 28, 1193
30. Yang, C.; Xia, W.-J. Chem.-Asian J. 2009, 4, 1774
31. Horspool, W. M. Synthetic Organic Photochemistry; Plenum Press: New York, 1984.
32. Xia, W.-J.; Shao, Y.-T.; Gui, W.-J.; Yang, C. Chem. Commun. 2011, 47, 11098
33. Liu, Q.; Meng, J.; Liu, Y.; Yang, C.; Xia, W.-J. J. Org. Chem. 2014, 79, 8143
34. Zhao, G.-L.; Yang, C.; Sun, H.-N.; Lin, R.; Xia, W.-J. Org. Lett. 2012, 14, 776
35. Shao, Y.-T.; Yang, C.; Gui, W.-J.; Liu, Y.; Xia, W.-J. Chem. Commun. 2012, 48, 3560
36. Gou, B.-Q.; Li, D.-Z.; Yang, C.; Xia, W.-J.; Li, Y.-L.; Chen, X.-M. J. Photochem. Photobiol. A: Chem. 2012, 233, 46
37. Yang, C.; Xia, W.-J.; Scheffer, J. R. Tetrahedron 2007, 63, 6791
38. Zhao, G.-L.; Yang, C.; Chen, Q.; Jin, J.; Zhang, X.; Zhao, L.-Y.; Xia, W.-J. Tetrahedron 2009, 65, 9952
39. Ayitou, A. J. L.; Sivaguru, J. J. Am. Chem. Soc. 2009, 131, 5036
40. CCDC 1026351 (6a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif (see the SI).