Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(15): 2466-2470
DOI: 10.1055/s-0030-1260095
DOI: 10.1055/s-0030-1260095
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Oxidative Addition of 1,3-Dicarbonyl Compounds to Terminal Acetylenes Mediated by Cerium(IV) Ammonium Nitrate
Further Information
Received
21 March 2011
Publication Date:
07 July 2011 (online)
Publication History
Publication Date:
07 July 2011 (online)
Abstract
Cerium(IV) ammonium nitrate mediated oxidative addition of 1,3-dicarbonyl compounds to terminal acetylenes to yield multisubstituted furan derivatives is reported here. The simplicity of the reaction and the ease of execution are particularly noteworthy.
Key words
cerium(IV) ammonium nitrate - oxidative addition - terminal acetylenes - multisubstituted furans - 1,3-dicarbonyl compounds
- For selected reviews, see:
-
1a
Lipshutz BH. Chem. Rev. 1986, 86: 795 -
1b
Lee HK.Chan KF.Hui CW.Yim HK.Wu XW.Wong HNC. Pure Appl. Chem. 2005, 77: 139 - For selected reviews, see:
-
2a
Hou XL.Yang Z.Wong HNC. Prog. Heterocycl. Chem. 2008, 19: 176 -
2b
Keay BA.Dibble PW. In Comprehensive Heterocyclic Chemistry II Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Elsevier; Oxford: 1997. p.395 -
3a
Brown RCD. Angew. Chem. Int. Ed. 2005, 44: 850 ; and references cited therein -
3b
Kirsch SF. Org. Biomol. Chem. 2006, 4: 2076 ; and references cited therein -
3c
Kao TT.Syu S.Jhang YW.Lin W. Org. Lett. 2010, 12: 3066 - 4
Baciocchi E.Ruzziconi R. Synth. Commun. 1988, 18: 1841 -
5a
Nair V.Deepthi A. Tetrahedron 2009, 65: 10745 -
5b
Nair V.Deepthi A. Chem. Rev. 2007, 107: 1862 -
6a
Sridharan V.Menendez JC. Chem. Rev. 2010, 110: 3805 -
6b
Nair V.Balagopal L.Rajan R.Mathew J. Acc. Chem. Res. 2004, 37: 21 -
6c
Nair V.Panicker SB.Nair LG.George TG.Augustine A. Synlett 2003, 156 - 7
Nair V.Mathew J. J. Chem. Soc., Perkin Trans. 1 1995, 187 - 8
Lee YR.Kang KY.Lee GJ.Lee WK. Synthesis 2003, 1977 -
9a
Yin J.Sommermann T.Linker T. Chem. Eur. J. 2007, 13: 10152 -
9b
Elamparuthi E.Kim BG.Yin J.Maurer M.Linker T. Tetrahedron 2008, 64: 11925 -
9c
Linker T.Schanzenbach D.Elamparuthi E.Sommermann T.Fudickar W.Gyóllai V.Somsák L.Dimuth W.Schmittel M. J. Am. Chem. Soc. 2008, 130: 16003 - 10
Nair V.Suja TD.Mohanan K. Synthesis 2006, 2335 -
11a
Kobayashi K.Mori M.Umed T.Morikawa O.Konishi H. Chem. Lett. 1996, 451 -
11b
Nair V.Treesa PM.Maliakal D.Rath NP. Tetrahedron 2001, 57: 7705 - 12
Kobayashi K.Tanaka H.Tanaka K.Yoneda K.Morikawa O.Konishi H. Synth. Commun. 2000, 30: 4277 -
13a
Wille U. J. Am. Chem. Soc. 2002, 124: 14 -
13b
Jargstorff C.Wille U. Eur. J. Org. Chem. 2003, 3173 -
13c
Dreessen T.Jargstorff C.Lietzau L.Plath C.Stademann A.Wille U. Molecules 2004, 9: 480