Facile aerobic photo-oxidative synthesis of α-diketones from alkynes

Tetrahedron Letters

Volumn 52, Issue 8, 2011, Pages 875-877

  Nobuta, Tomoya ^a   Tada, Norihiro ^a   Hattori, Kasumi ^a   Hirashima, Shin Ichi ^a   Miura, Tsuyoshi ^a   Itoh, Akichika ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Diketones; Aerobic; Alkynes; MgBr2 OEt2; Photo oxidation

Indexed keywords

1,2 DICARBONYL DERIVATIVE; ALKYNE; BROMINE DERIVATIVE; OXIDIZING AGENT; OXYGEN;

ARTICLE; LIGHT; PHOTOOXIDATION; SYNTHESIS;

EID: 78751567737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.029     Document Type: Article

References (29)

1. M. Venkatachalam, M.N. Deshpande, M. Jawdosiuk, G. Kubiak, S. Wehrli, and J.M. Cook Tetrahedron 42 1986 1597 1605
2. Z. Zhao, W.H. Leister, K.A. Strauss, D.D. Wisnoski, and C.W. Lindsley Tetrahedron Lett. 44 2003 1123 1127
3. Z. Zhao, D.D. Wisnoski, S.E. Wolkenberg, W.H. Leister, Y. Wang, and C.W. Lindsley Tetrahedron Lett. 45 2004 4873 4876
4. S.E. Wolkenberg, D.D. Wisnoski, W.H. Leister, Y. Wang, Z. Zhao, and C.W. Lindsley Org. Lett. 6 2004 1453 1456
5. D.G. Lee, and V.S. Chang Synthesis 1978 462 463
6. D.G. Lee, E.J. Lee, and W.D. Chandler J. Org. Chem. 50 1985 4306 4309
7. W.B. Sheats, L.K. Olli, R. Stout, J.T. Lundeen, R. Justus, and W.G. Nigh J. Org. Chem. 44 1979 4075 4078
8. H. Gopal, and A.J. Gordon Tetrahedron Lett. 31 1971 2941 2944
9. P. Müller, and J. Godoy Helv. Chim. Acta 64 1981 2531 2533
10. C.-M. Che, W.-Y. Yu, P.-M. Chan, W.-C. Cheng, S.-M. Peng, K.-C. Lau, and W.-K. Li J. Am. Chem. Soc. 122 2000 11380 11392
11. W. Ren, J. Liu, L. Chen, and X. Wan Adv. Synth. Catal. 352 2010 1424 1428
12. Z. Zhu, and J.H. Espenson J. Org. Chem. 60 1995 7728 7732
13. K.-W. Chi, M.S. Yusubov, and V.D. Filimonov Synth. Commun. 24 1994 2119 2122
14. W. Ren, Y. Xia, S.-J. Ji, Y. Zhang, X. Wan, and J. Zhao Org. Lett. 11 2009 1841 1844
15. M.S. Yusubov, and V.D. Filimonov Synthesis 1991 131 132
16. M.S. Yusubov, V.D. Filimonov, V.P. Vasilyeva, and K.-W. Chi Synthesis 1995 1234 1236
17. Z. Wan, C.D. Jones, D. Mitchell, J.Y. Pu, and T.Y. Zhang J. Org. Chem. 71 2006 826 828
18. J.-H. Chu, Y.-J. Chen, and M.-J. Wu Synthesis 2009 2155 2162
19. M. Niu, H. Fu, Y. Jiang, and Y. Zhao Synthesis 2008 2879 2882
20. C. Aronovitch, D. Tal, and Y. Mazur Tetrahedron Lett. 35 1982 3623 3626
21. S. Dayan, I. Ben-David, and S. Rozen J. Org. Chem. 65 2000 8816 8818
22. S. Hirashima, and A. Itoh Green. Chem. 9 2007 318 320
23. S. Hirashima, and A. Itoh Photochem. Photobiol. Sci. 6 2007 521
24. S. Hirashima, and A. Itoh J. Synth. Org. Chem. Jpn. 66 2008 748 756
25. 3 and brine, concentrated in vacuo, and purified by PTLC.
26. 2 was probably trapped by triple bond of diphenylacetylene (1) and the reaction did not proceed efficiently.
27. 300 W Xenon lamp (ASAHI SPECTRA MAX-301) was used.
28. The reaction did not proceed when 1.0 equiv of galvinoxyl, which is a radical scavenger, was added.
29. S. Fukuzumi, and K. Ohkubo Chem. Eur. J. 6 2000 4532 4535