Oxidative rearrangement of internal alkynes to give one-carbon-shorter ketones via manganese porphyrins catalysis

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5691-5693

  Sheng, Wen Bing ^a,b   Jiang, Qing ^a   Luo, Wei Ping ^a   Guo, Can Cheng ^a  

^a HUNAN UNIVERSITY   (China)

^b HUNAN UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; HYDROCARBONS; KETONES; MOLECULAR OXYGEN; PORPHYRINS;

DIARYLALKYNES; HIGH YIELD; INTERNAL ALKYNES; MANGANESEPORPHYRINS; OXIDATIVE REARRANGEMENTS; REACTION MECHANISM; STANDARD CONDITIONS;

MANGANESE COMPOUNDS;

ALKYNE DERIVATIVE; CARBON; KETONE DERIVATIVE; MANGANESE PORPHYRIN DERIVATIVE; OXYGEN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; EPOXIDATION; OXIDATION; OXIDATIVE REARRANGEMENT; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84879291019     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400209p     Document Type: Article

References (37)

1. Ishii, Y.; Sakata, Y. J. Org. Chem. 1990, 55, 5545-5547
2. Chandrasekhar, S.; Reddy, N. K.; Kumar, V. P. Tetrahedron Lett. 2010, 51, 3623-3625
3. Ren, W.; Xia, Y.; Ji, S. J.; Zhang, Y.; Wan, X.; Zhao, J. Org. Lett. 2009, 11, 1841-1844
4. Zeller, K. P.; Kowallik, M.; Haiss, P. Org. Biomol. Chem. 2005, 3, 2310-2318
5. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7728-7732
6. Che, C. M.; Yu, W. Y.; Chan, P. M.; Cheng, W. C.; Peng, S. M.; Lau, K. C.; Li, W. K. J. Am. Chem. Soc. 2000, 122, 11380-11392
7. Ren, W.; Liu, J.; Chen, L.; Wan, X. Adv. Synth. Catal. 2010, 352, 1424-1428
8. Chu, J. H.; Chen, Y. J.; Wu, M. J. Synthesis 2009, 13, 2155-2162
9. Ryu, J. Y.; Heo, S.; Park, P.; Nam, W.; Kim, J. Inorg. Chem. Commun. 2004, 7, 534-537
10. Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1983, 105, 7755-7757
11. Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature (London, U. K.) 2011, 471, 461-466
12. Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 154-1585
13. O'Neil, G. W.; Ceccon, J.; Benson, S.; Collin, M. P.; Fasching, B.; Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 9940-9945
14. Jun, C. H.; Lee, H.; Moon, C. W.; Gong, H. S. J. Am. Chem. Soc. 2001, 123, 8600-8601
15. Lee, D. Y.; Hong, B. S.; Cho, E. G.; Lee, H.; Jun, C. H. J. Am. Chem. Soc. 2001, 125, 6372-6373
16. Lee, K.; Kim, Y. H.; Han, S. B.; Kang, H.; Park, S.; Seo, W. S.; Park, J. T.; Kim, B.; Chang, S. J. Am. Chem. Soc. 2003, 125, 6844-6845
17. Wang, A.; Jiang, H. J. Am. Chem. Soc. 2008, 130, 5030-5031
18. Shaikh, T. M.; Hong, F. E. Adv. Synth. Catal. 2011, 353, 1491-1496
19. Muzart, J. J. Mol. Catal. A: Chem. 2011, 338, 7-17
20. Pirguliyev, N. S.; Brel, V. K.; Zefirov, N. S.; Stang, P. J. Mendeleev Commun. 1999, 9, 189-190
21. Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Vaid, B. K. Tetrahedron Lett. 1987, 28, 2845-2848
22. Dayan, S.; David, I. B.; Rozen, S. J. Org. Chem. 2000, 65, 8816-8818
23. Jun, C. H. Chem. Soc. Rev. 2004, 33, 610-618
24. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769
25. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759-1792
26. The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilar, R., Eds.; Academic Press: San Diego, 1999; Vol. 4, pp 119-144.
27. Liu, Q.; Guo, C. C. Sci. China Chem. 2012, 55, 2036-2053
28. Guo, C. C.; Liu, X. Q.; Liu, Q.; Liu, Y.; Chu, M. F.; Liu, M. Y. J. Porphyrins Phthalocyanines 2009, 13, 1250-1254
29. Guo, C. C.; Zhu, S. J.; Gui, M. D. Acta Chim. Sin. 1992, 50, 129-134
30. Guo, C. C. J. Catal. 1998, 178, 182-187
31. Guo, C. C.; Song, J. X.; Chen, X. B.; Jiang, G. F. J. Mol. Catal. A: Chem. 2000, 157, 31-40
32. Meier, H.; Zeller, K. P. Angew. Chem., Int. Ed. Engl. 1975, 14, 32-43
33. Wille, U.; Andropof, J. Aust. J. Chem. 2007, 60, 420-428
34. Ciabattoni, J.; Campbell, R. A.; Renner, C. A.; Concannon, P. W. J. Am. Chem. Soc. 1970, 92, 3826-3828
35. Lewars, E. G. Chem. Rev. 1983, 83, 519-534
36. Sawant, D. N.; Tambade, P. J.; Wagh, Y. S.; Bhanage, B. M. Tetrahedron Lett. 2010, 51, 2758-2761
37. Yang, D. S.; Li, B.; Yang, H. J.; Fu, H.; Hu, L. Synlett 2011, 5, 702-706