A new and efficient method for the synthesis of α,α- dihaloketones by oxyhalogenation of alkynes using oxone®-KX (X = Cl, Br, or I)

Tetrahedron Letters

Volumn 54, Issue 30, 2013, Pages 3993-3996

  Madabhushi, Sridhar ^a   Jillella, Raveendra ^a   Mallu, Kishore Kumar Reddy ^a   Godala, Kondal Reddy ^a   Vangipuram, Venkata Sairam ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

, Dihaloketones; Alkynes; Oxone ; Oxyhalogenation; Potassium halide

Indexed keywords

ALKYNE DERIVATIVE; KETONE DERIVATIVE; SODIUM PEROXIDE;

ARTICLE; HALOGENATION; OXYGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84879422878     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.072     Document Type: Article

References (35)

1. G.A. Olah, K.K. Laali, Q. Wang, and G.K.S. Prakash Onium Ions 1998 John Wiley & Sons New York
2. P.B.D. DeLaMare, and R. Bolton Electrophilic Additions to Unsaturated Systems 2nd ed. 1982 Elsevier New York
3. K. Kim, J. Cho, and S.C. Yoon J. Chem. Soc., Perkin Trans. 1 1995 253 259
4. C.J. Kowalski, and K.W. Fields J. Am. Chem. Soc. 104 1982 321 323
5. V.V. Zhdankin, and P.J. Stang Tetrahedron Lett. 34 1993 1461 1462
6. J. Fujiwara, A. Matsumura, Y. Matsuoka, and J. Kiji Bull. Chem. Soc. Jpn. 49 1976 829 831
7. N. Kawabata, T. Fuji, M. Naka, and S. Yamashita Bull. Chem. Soc. Jpn. 50 1977 1005 1015
8. W. Taylor J. Chem. Soc. 1937 304 308
9. M. Ghiaci, and J. Asghari Bull. Chem. Soc. Jpn. 74 2001 1151 1152
10. M.T. Rahman, N. Kamata, H. Matsubara, and I. Ryu Synlett 2005 2664 2666
11. C. Ye, and J.M. Shreeve J. Org. Chem. 69 2004 8561 8563
12. B. Floris, V. Conte, P. Galloni, and A. Silvagni Adv. Synth. Catal. 347 2005 1341 1344
13. Jinhua Li, Wenjuan Li, Wang Li, Yao Li, and Zhiping Li Tetrahedron Lett. 52 2011 4320 4323
14. T. Nobuta, S. Hirashima, N. Tada, T. Miura, and A. Itoh Tetrahedron Lett. 51 2010 4576 4578
15. S.E. Denmark, D.C. Forbes, D.S. Hays, J.S. DePue, and R.G. Wilde J. Org. Chem. 60 1995 1393 1407
16. H. Tian, X. She, and Y. Shi Org. Lett. 3 2001 715 718
17. A.S. Cavallo, and L. Bouerat Org. Lett. 2 2000 3531 3534
18. H. Tian, H. She, J. Xu, and Y. Shi Org. Lett. 3 2001 1929 1931
19. M.K. Wong, L.M. Ho, Y.S. Zheng, C. Yu Ho, and D. Yang Org. Lett. 3 2001 2587 2590
20. P.C. Bulman Page, B.R. Buckley, H. Heaney, and A.J. Blacker Org. Lett. 7 2005 2933 2936
21. K. Jakka, and C.G. Zhao Org. Lett. 8 2006 3013 3015
22. C.P. Burke, and Y. Shi Org. Lett. 22 2009 5150 5153
23. G. Cravotto, D. Garella, D. Carnaroglio, E.C. Gaudinoa, and O. Rosatib Chem. Commun. 2012 11632 11634
24. B.R. Travis, M. Sivakumar, G.O. Hollist, and B. Borhan Org. Lett. 5 2003 1031 1034
25. M.E. Brik Tetrahedron Lett. 36 1995 5519 5522
26. M.A. Kumar, C.N. Rohitha, S.J. Kulkarni, and N. Narender Synthesis 2010 1629 1632
27. M.A. Kumar, C.N. Rohitha, S.J. Kulkarni, and N. Narender Tetrahedron Lett. 53 2012 1401 1405
28. K. Moriyama, M. Takemura, and H. Togo Org. Lett. 14 2006 2414 2417
29. C.G. Swain, and D.R. Crist J. Am. Chem. Soc. 94 1972 3195 3200
30. C.A. Delcomyn, K.E. Bushway, and M.V. Henley Environ. Sci. Technol. 40 2006 2759 2764
31. F.A. Carey, and R.J. Sundeberg Advanced Organic Chemistry; Part A: Structure and Mechanism 4th ed. 2000 Kluwer Academic/Plenum Publishers New York pp 351-398
32. E. Wiberg, N. Wiberg, and A.F. Holleman Inorganic Chemistry, Section 4.3.1 2001 Academic Press p 442
33. S. Larson, T. Luidhardt, G.W. Kabalka, and R.M. Pagni Tetrahedron Lett. 29 1988 35 36
34. E.N. Tveryakova, Yu.Yu. Miroshnichenko, I.A. Perederina, and M.S. Yusubov Russ. J. Org. Chem. 43 2007 152 153
35. S.M. Al-Mousawi, I. Bhatti, and S.D. Saraf Org. Prep. Proced. Int. 24 1992 60 63