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Synthesis 2008(18): 2879-2882
DOI: 10.1055/s-2008-1067240
DOI: 10.1055/s-2008-1067240
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Convenient and Practical Approach to α-Diketones via Reactions of Internal Aryl Alkynes with N-Iodosuccinimide/Water
Further Information
Received
17 April 2008
Publication Date:
22 August 2008 (online)
Publication History
Publication Date:
22 August 2008 (online)
Abstract
A convenient and practical approach to α-diketones via reactions of alkynes with N-iodosuccinimides/water at 70 ˚C has been developed.
Key words
α-diketones - alkynes - N-iodosuccinimide - convenient and practical - water
-
1a
Babudri F.Fiandanese V.Marchese G.Punzi A. Tetrahedron Lett. 1995, 40: 7305 ; and references therein -
1b
De Kimpe N.Stanoeva E.Boeykens M. Synthesis 1994, 427 ; and references therein -
2a
Barta TE.Stealey MA.Collins PW.Weier RM. Bioorg. Med. Chem. Lett. 1998, 8: 3443 -
2b
Zhao ZJ.Wisnoski DD.Wolkenberg SE.Leister WH.Wang Y.Lindsley CW. Tetrahedron Lett. 2004, 45: 4873 -
2c
Held I.Xu SJ.Zipse H. Synthesis 2007, 1185 -
2d
Rong F.Chow S.Yan SQ.Larson G.Hong Z.Wu J. Bioorg. Med. Chem. Lett. 2007, 17: 1663 -
3a
Bibaut-Renauld C.Burget D.Fouassier JP.Varelas CG.Thomatos J.Tsagaropoulos G.Ryrfors LO.Karlsson OJ. J. Polym. Sci., Part A: Polym. Chem. 2002, 40: 3171 -
3b
Ams MR.Wilcox CS. J. Am. Chem. Soc. 2007, 129: 3966 -
4a
Casey CP.Guan H. J. Am. Chem. Soc. 2007, 129: 5816 -
4b
Procuranti B.Connon SJ. Chem. Commun. 2007, 14: 1421 -
5a
Naoki K.Nasuo U. Bull. Chem. Soc. Jpn. 2001, 74: 755 -
5b
Katritzky AR.Zhang DZ.Kirichenko K. J. Org. Chem. 2005, 70: 3271 ; and references therein -
6a
Srinvasan NS.Lee DG. J. Org. Chem. 1979, 44: 1574 -
6b
Lee DG.Chang VS. Synthesis 1978, 6: 462 -
7a
Wolfe S.Pilgrim WR.Garrad TF.Chamberlain P. Can. J. Chem. 1971, 49: 1099 -
7b
Yusybov MS.Filimonov VD. Synthesis 1991, 131 -
7c
Chi KW.Yusubov MS.Filimonov VD. Synth. Commun. 1994, 24: 2119 -
7d
Foster EJ.Babuin J.Nguyen N.Williams VE. Chem. Commun. 2004, 18: 2052 -
8a
McDonald RN.Schwab PA. J. Am. Chem. Soc. 1964, 86: 4866 -
8b
Aronovitch C.Tal D.Mazur Y. Tetrahedron Lett. 1982, 23: 3623 -
9a
Sheats WB.Olli LK.Stout R.Lundeen JT.Justus R.Nigh WG. J. Org. Chem. 1979, 44: 4075 -
9b
Che CM.Yu WY.Chan PM.Cheng WC.Peng SM.Lau KC.Li WK. J. Am. Chem. Soc. 2000, 122: 11380 -
9c
Giraud A.Provot O.Peyrat J.-F.Alami M.Brion J.-D. Tetrahedron 2006, 62: 7667 -
9d
Tummatorn J.Khorphueng P.Petsom A.Muangsin N.Chaichitc N.Roengsumran S. Tetrahedron 2007, 63: 11878 -
10a
Dayan S.Ben-David I.Rozen S. J. Org. Chem. 2000, 65: 8816 -
10b
Wan ZH.Jones CD.Mitchell D.Pu JY.Zhang TY. J. Org. Chem. 2006, 71: 826 -
11a
Reed SF. J. Org. Chem. 1965, 30: 2195 -
11b
Heasley VL.Shellhamer DF.Chappell AE.Cox JM.Hill DJ.McGovern SL.Eden CC. J. Org. Chem. 1998, 63: 4433 - 12
Takahashi S.Kuroyama Y.Sonogashira K.Hagihara N. Synthesis 1980, 627 - 13
Chaikovskii VK.Skorokhodov VI.Filimonov VD. Russ. J. Org. Chem. 2001, 37: 1572 - 14
Tiecco M.Testaferri L.Tingoli M.Chianelli D.Bartoli D. J. Org. Chem. 1991, 56: 4529 - 15
Noh T.Choi K.Kwon H.Chang DJ.Park BS. Bull. Korean Chem. Soc. 1999, 20: 539 - 16
Yi XB.Wu GS.Lu FC. Chin. J. Polym. Sci. 2002, 20: 219 - 17
Yamamori T.Adachi I. Tetrahedron Lett. 1980, 21: 1747 - 18
Chang CL.Kumar MP.Liu RS. J. Org. Chem. 2004, 69: 2793 - 19
Correia J. J. Org. Chem. 1992, 57: 4555 - 20
Nobrega JA.Goncalves SMC.Peppe C. Synth. Commun. 2002, 32: 3711