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 2010(20): 3415-3417
DOI: 10.1055/s-0030-1258211
DOI: 10.1055/s-0030-1258211
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Use of Ionic Liquid as Solvent in the Oxidation of Furans with Singlet Oxygen
Further Information
Received
8 July 2010
Publication Date:
13 August 2010 (online)
Publication History
Publication Date:
13 August 2010 (online)
Abstract
The photocatalytic oxidation of a furan to a hydroxybutenolide in good yield is the first step of a one-pot synthesis of a γ-substituted α,β-unsaturated γ-butyrolactone in the ionic liquid 1-hexyl-3-methylimidazolium chloride ([HMIM][Cl]).
Key words
ionic liquids - singlet oxygen oxidation - butenolide synthesis
-
1a
Prein M.Adam W. Angew. Chem., Int. Ed. Engl. 1996, 35: 477 -
1b
Clennan EL. Tetrahedron 2000, 56: 9151 -
1c
Paquette LA.Tac J.Arrington MP.Sadoun AH. J. Am. Chem. Soc. 2000, 122: 2742 -
1d
Adam W.Saha-Möller CR.Schmid KS. J. Org. Chem. 2001, 66: 7365 -
1e
Vassilikogiannakis G.Stratakis M. Angew. Chem. Int. Ed. 2003, 42: 5465 -
1f
Clennan EL.Pace A. Tetrahedron 2005, 61: 6665 -
1g
Vassilikogiannakis G.Margaros I.Montagnon T.Stratakis M. Chem. Eur. J. 2005, 11: 5899 -
1h
Margaros I.Montagnon T.Tofi M.Pavlakos E.Vassilikogiannakis G. Tetrahedron 2006, 62: 5308 -
1i
Alberti MN.Orfanopoulos M. Tetrahedron 2006, 62: 10660 -
2a
Fall Y.Vidal B.Alonso D.Gómez G. Tetrahedron Lett. 2003, 44: 4467 -
2b
Pérez M.Canoa P.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2004, 45: 5207 -
2c
Alonso D.Pérez M.Gómez G.Covelo B.Fall Y. Tetrahedron 2005, 61: 2021 -
2d
Teijeira M.Suárez PL.Gómez G.Terán C.Fall Y. Tetrahedron Lett. 2005, 46: 5889 -
2e
García I.Gómez G.Teijeira M.Terán C.Fall Y. Tetrahedron Lett. 2006, 47: 1333 -
2f
Canoa P.Pérez M.Covelo B.Gómez G.Fall Y. Tetrahedron Lett. 2007, 48: 3441 -
2g
Canoa P.Vega N.Pérez N.Gómez G.Fall Y. Tetrahedron Lett. 2008, 49: 1149 -
2h
García I.Pérez M.Besada P.Gómez G.Fall Y. Tetrahedron Lett. 2008, 49: 1344 - 3
Gómez G.Rivera H.García I.Estevez L.Fall Y. Tetrahedron Lett. 2005, 46: 5819 - 4
García I.Pérez M.Gándara Z.Gómez G.Fall Y. Tetrahedron Lett. 2008, 49: 3609 -
5a
Boullosa S.Gándara Z.Pérez M.Gómez G.Fall Y. Tetrahedron Lett. 2008, 49: 4040 -
5b
Besada P.Pérez M.Gómez G.Fall Y. Tetrahedron Lett. 2009, 50: 6941 - For recent reviews on ionic liquids, see:
-
6a
Welton T. Chem. Rev. 1999, 99: 2071 -
6b
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
6c
Sheldon R. Chem. Commun. 2001, 2399 -
6d
Wilkes JS. Green Chem. 2002, 4: 73 -
6e
Scammells PJ.Scott JL.Singer RD. Aust. J. Chem. 2005, 58: 155 -
6f
Bica K.Gaertner P. Eur. J. Org. Chem. 2008, 3235 - 7
Teijeira M.Fall Y.Santamarta F.Tojo E. Tetrahedron Lett. 2007, 48: 7926 -
8a
Marcos IS.Castañeda L.Basabe P.Díez D.Urones JG. Tetrahedron 2009, 65: 9256 -
8b
Basabe P.Bodero O.Marcos IS.Díez D.Blanco A.de Román M.Urones JG. J. Org. Chem. 2009, 74: 7750 -
8c
Montagnon T.Tofi M.Vassilikogiannakis G. Acc. Chem. Res. 2008, 41: 1001 -
8d
Margaros I.Vassilikogiannakis G. J. Org. Chem. 2007, 72: 4826 -
8e
Margaros I.Montagnon T.Tofi M.Pavlakos E.Vassilikogiannakis G. Tetrahedron 2006, 62: 5308 -
8f
Vassilikogiannakis G.Stratakis M. Angew. Chem. Int. Ed. 2003, 42: 5465 -
8g
Corey EJ.Roberts BE. J. Am. Chem. Soc. 1997, 119: 12425 - 9
Kern MR.Faulkner DJ. J. Org. Chem. 1988, 53: 2773 -
10a
Swiderski K.McLean A.Gordon CM.Vaughan DH. Chem. Commun. 2004, 2178 -
10b
Gandra N.Frank AT.Le Gendre O.Sawwan N.Aebisher D.Liebman JF.Houk KN.Greer A.Gao R. Tetrahedron 2006, 62: 10771 -
10c
Baciocchi E.Chiappe C.Del Giacco T.Fasciani C.Lanzalunga O.Lapi A.Melai B. Org. Lett. 2009, 11: 1413 -
10d
Astarita A.Cermola F.DellaGreca M.Iesce MR.Previtera L.Rubino M. Green Chem. 2009, 11: 2030 - 11
Gao P.Tong Z.Hu H.Xu P.-F.Liu W.Sun C.Zhai H. Synlett 2009, 2188 - 12
Hanessian S.Hodges PJ.Murray PJ.Sahoo SP.
J. Chem. Soc., Chem. Commun. 1986, 754 - 13
Pereiro AB.Santamarta F.Tojo E.Rodríguez A.Tojo J. J. Chem. Eng. Data 2006, 51: 952 - 14
Gómez E.González B.Dominguez A.Tojo E.Tojo J. J. Chem. Eng. Data 2006, 51: 696 - 15
Holbrey JD.Seddon KR. J. Chem. Soc., Dalton Trans. 1999, 2133 - 16
Wu W.Han B.Gao H.Liu Z.Jiang T.Huang J. Angew. Chem. Int. Ed. 2004, 43: 2415