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Synthesis 2009(12): 1969-1974
DOI: 10.1055/s-0029-1216825
DOI: 10.1055/s-0029-1216825
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Highly Efficient and Reusable Ionic Liquids for the Catalyzed Hydroamination of Alkenes with Sulfonamides, Carbamates, and Carboxamides
Further Information
Received
20 January 2009
Publication Date:
19 May 2009 (online)
Publication History
Publication Date:
19 May 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200912/lookinside/thumbnails/10.1055-s-0029-1216825-1.jpg)
Abstract
SO3H-Functionalized ionic liquids were found to be efficient and reusable catalysts in the hydroamination of sulfonamides, carboxamides, p-nitroaniline and carbamates with nonactivated alkenes. The hydroamination could be performed on a large scale and the acidic ionic liquid catalyst could be reused successfully.
Key words
hydroamination - ionic liquid - green chemistry - alkene - homogeneous catalysis
- 1
Roundhill DM. Chem. Rev. 1992, 92: 1 -
2a
Müller TE.Beller M. Chem. Rev. 1998, 98: 675 -
2b
Roesky PW.Müller TE. Angew. Chem. Int. Ed. 2003, 42: 2708 -
2c
Bystschkov I.Doye S. Eur. J. Org. Chem. 2003, 935 -
2d
Hultzsch KC. Adv. Synth. Catal. 2005, 347: 367 -
2e
Severin R.Doye S. Chem. Soc. Rev. 2007, 36: 1407 -
3a
Qian H.Widenhoefer RA. Org. Lett. 2005, 7: 2635 -
3b
Karshtedt D.Bell AT.Tilley TD. J. Am. Chem. Soc. 2005, 127: 12640 -
4a
Zhang JL.Yang CG.He C. J. Am. Chem. Soc. 2006, 128: 1798 -
4b
Liu XY.Li C.Che CM. Org. Lett. 2006, 8: 2707 -
4c
Bender CF.Widenhoefer RA. Org. Lett. 2006, 8: 5303 -
4d
Brouwer C.He C. Angew. Chem. Int. Ed. 2006, 45: 1744 - 5
Taylor JG.Whittall N.Hii KK. Org. Lett. 2006, 8: 3561 - 6
Michaux J.Terrasson V.Marque S.Wehbe J.Prim D.Campagne JM. Eur. J. Org. Chem. 2007, 2601 -
7a
Huang JM.Wong CM.Xu FX.Loh TP. Tetrahedron Lett. 2007, 48: 3375 -
7b
Qin H.Yamagiwa N.Matsunaga S.Shibasaki M. Chem. Asian J. 2007, 2: 150 -
7c
Qin H.Yamagiwa N.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2006, 128: 1611 -
8a
Talluri SK.Sudalai A. Org. Lett. 2005, 7: 855 -
8b
Li Z.Zhang J.Brouwer C.Yang CG.Reich NW.He C. Org. Lett. 2006, 8: 4175 -
8c
Rosenfeld DC.Shekhar S.Takemiya A.Utsunomiya M.Hartwig JF. Org. Lett. 2006, 8: 4179 -
8d
Motokura K.Nakagiri N.Mori K.Mizugaki K.Ebitani T.Jitsukawa K.Kaneda K. Org. Lett. 2006, 8: 4617 - 9 Special issue on ionic liquids Acc. Chem. Res. 2007, 40: 1077-1236
-
10a
Bates ED.Mayton RD.Ntai I.Davis JH. J. Am. Chem. Soc. 2002, 124: 926 -
10b
Kitaoka S.Nobuoka K.Ishikawa Y. Chem. Commun. 2004, 1902 -
10c
Zhao G.Jiang T.Gao H.Han B.Huang J.Sun D. Green Chem. 2004, 6: 75 -
10d
Gu Y.Zhang J.Duan Z.Deng Y. Adv. Synth. Catal. 2005, 347: 512 -
11a
Brunet JJ.Chu NC.Diallo O.Vincendeau S. J. Mol. Catal. A: Chem. 2005, 240: 245 -
11b
Bodis J.Müller TE.Lercher JA. Green Chem. 2003, 5: 227 -
11c
Lapis AAM.DaSilveira Neto BA.Scholten JD.Nachtigall FM.Eberlin MN.Dupont J. Tetrahedron Lett. 2006, 47: 6775 -
11d
Jimenez O.Müller TE.Sievers C.Spirkl A.Lercher JA. Chem. Commun. 2006, 2974 -
11e
Fadini L.Togni A. Helv. Chim. Acta 2007, 90: 411 -
11f
Brunet JJ.Chu NC.Rodriguez-Zubiri M. Eur. J. Inorg. Chem. 2007, 4711 -
11g
Sievers C.Jimenez O.Knapp R.Lin XL.Müller TE.Türler A.Wierczinski B.Lercher JA. J. Mol. Catal. A: Chem. 2008, 279: 187 -
12a
Xu LW.Li JW.Zhou SL.Xia CG. New J. Chem. 2004, 28: 183 -
12b
Xu LW.Gao Y.Yin JJ.Li L.Xia CG. Tetrahedron Lett. 2005, 46: 5317 -
12c
Yang L.Xu LW.Zhou W.Li L.Xia CG. Tetrahedron Lett. 2006, 47: 7723 -
13a
Xu LW.Xia CG.Hu XX. Chem. Commun. 2003, 2570 -
13b
Xu LW.Xia CG. Eur. J. Org. Chem. 2005, 633 -
13c
Yang L.Xu LW.Xia CG. Tetrahedron Lett. 2007, 48: 1599 -
13d
Yang L.Xu LW.Xia CG. Tetrahedron Lett. 2008, 49: 2882 -
14a
Zhu HP.Yang F.Tang J.He MY. Green Chem. 2003, 5: 38 -
14b
Gu Y.Shi F.Deng Y. J. Mol. Catal. A: Chem. 2004, 212: 71 -
14c
Fraga-Dubreuil J.Bourahla K.Rahmouni M.Bazureau JP.Hamelin J. Catal. Commun. 2002, 3: 185 -
14d
Cole AC.Jensen JL.Ntai I.Tran KLT.Weaver KJ.Forbes DC.Davis JH. J. Am. Chem. Soc. 2002, 124: 5962