Highly Efficient and Reusable
Ionic Liquids for the Catalyzed Hydro­amination of Alkenes
with Sulfonamides, Carbamates, and Carboxamides

Lei Yang; Li-Wen Xu; Chun-Gu Xia

doi:10.1055/s-0029-1216825

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Synthesis 2009(12): 1969-1974
DOI: 10.1055/s-0029-1216825

PAPER

Highly Efficient and Reusable Ionic Liquids for the Catalyzed Hydroamination of Alkenes with Sulfonamides, Carbamates, and Carboxamides

Lei Yang^a, Li-Wen Xu*^a,b, Chun-Gu Xia*^a
^a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, and Graduate School of the Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
Fax: +86(931)8277088; e-Mail: lyang@lzb.ac.cn; e-Mail: cgxia@lzb.ac.cn;
^b Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, P. R. of China

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Publication History

Received 20 January 2009
Publication Date:
19 May 2009 (online)

Abstract
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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

References

1 Roundhill DM. Chem. Rev. 1992, 92: 1

Crossref Google Scholar
2a Müller TE. Beller M. Chem. Rev. 1998, 98: 675

Google Scholar
2b Roesky PW. Müller TE. Angew. Chem. Int. Ed. 2003, 42: 2708

Google Scholar
2c Bystschkov I. Doye S. Eur. J. Org. Chem. 2003, 935

Google Scholar
2d Hultzsch KC. Adv. Synth. Catal. 2005, 347: 367

Google Scholar
2e Severin R. Doye S. Chem. Soc. Rev. 2007, 36: 1407

Google Scholar
3a Qian H. Widenhoefer RA. Org. Lett. 2005, 7: 2635

Google Scholar
3b Karshtedt D. Bell AT. Tilley TD. J. Am. Chem. Soc. 2005, 127: 12640

Google Scholar
4a Zhang JL. Yang CG. He C. J. Am. Chem. Soc. 2006, 128: 1798

Google Scholar
4b Liu XY. Li C. Che CM. Org. Lett. 2006, 8: 2707

Google Scholar
4c Bender CF. Widenhoefer RA. Org. Lett. 2006, 8: 5303

Google Scholar
4d Brouwer C. He C. Angew. Chem. Int. Ed. 2006, 45: 1744

Google Scholar
5 Taylor JG. Whittall N. Hii KK. Org. Lett. 2006, 8: 3561

Crossref PubMed Google Scholar
6 Michaux J. Terrasson V. Marque S. Wehbe J. Prim D. Campagne JM. Eur. J. Org. Chem. 2007, 2601

Crossref Google Scholar
7a Huang JM. Wong CM. Xu FX. Loh TP. Tetrahedron Lett. 2007, 48: 3375

Google Scholar
7b Qin H. Yamagiwa N. Matsunaga S. Shibasaki M. Chem. Asian J. 2007, 2: 150

Google Scholar
7c Qin H. Yamagiwa N. Matsunaga S. Shibasaki M. J. Am. Chem. Soc. 2006, 128: 1611

Google Scholar
8a Talluri SK. Sudalai A. Org. Lett. 2005, 7: 855

Google Scholar
8b Li Z. Zhang J. Brouwer C. Yang CG. Reich NW. He C. Org. Lett. 2006, 8: 4175

Google Scholar
8c Rosenfeld DC. Shekhar S. Takemiya A. Utsunomiya M. Hartwig JF. Org. Lett. 2006, 8: 4179

Google Scholar
8d Motokura K. Nakagiri N. Mori K. Mizugaki K. Ebitani T. Jitsukawa K. Kaneda K. Org. Lett. 2006, 8: 4617

Google Scholar
9 Special issue on ionic liquids Acc. Chem. Res. 2007, 40: 1077-1236

Crossref Google Scholar
10a Bates ED. Mayton RD. Ntai I. Davis JH. J. Am. Chem. Soc. 2002, 124: 926

Google Scholar
10b Kitaoka S. Nobuoka K. Ishikawa Y. Chem. Commun. 2004, 1902

Google Scholar
10c Zhao G. Jiang T. Gao H. Han B. Huang J. Sun D. Green Chem. 2004, 6: 75

Google Scholar
10d Gu Y. Zhang J. Duan Z. Deng Y. Adv. Synth. Catal. 2005, 347: 512

Google Scholar
11a Brunet JJ. Chu NC. Diallo O. Vincendeau S. J. Mol. Catal. A: Chem. 2005, 240: 245

Google Scholar
11b Bodis J. Müller TE. Lercher JA. Green Chem. 2003, 5: 227

Google Scholar
11c Lapis AAM. DaSilveira Neto BA. Scholten JD. Nachtigall FM. Eberlin MN. Dupont J. Tetrahedron Lett. 2006, 47: 6775

Google Scholar
11d Jimenez O. Müller TE. Sievers C. Spirkl A. Lercher JA. Chem. Commun. 2006, 2974

Google Scholar
11e Fadini L. Togni A. Helv. Chim. Acta 2007, 90: 411

Google Scholar
11f Brunet JJ. Chu NC. Rodriguez-Zubiri M. Eur. J. Inorg. Chem. 2007, 4711

Google Scholar
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

Google Scholar
12a Xu LW. Li JW. Zhou SL. Xia CG. New J. Chem. 2004, 28: 183

Google Scholar
12b Xu LW. Gao Y. Yin JJ. Li L. Xia CG. Tetrahedron Lett. 2005, 46: 5317

Google Scholar
12c Yang L. Xu LW. Zhou W. Li L. Xia CG. Tetrahedron Lett. 2006, 47: 7723

Google Scholar
13a Xu LW. Xia CG. Hu XX. Chem. Commun. 2003, 2570

Google Scholar
13b Xu LW. Xia CG. Eur. J. Org. Chem. 2005, 633

Google Scholar
13c Yang L. Xu LW. Xia CG. Tetrahedron Lett. 2007, 48: 1599

Google Scholar
13d Yang L. Xu LW. Xia CG. Tetrahedron Lett. 2008, 49: 2882

Google Scholar
14a Zhu HP. Yang F. Tang J. He MY. Green Chem. 2003, 5: 38

Google Scholar
14b Gu Y. Shi F. Deng Y. J. Mol. Catal. A: Chem. 2004, 212: 71

Google Scholar
14c Fraga-Dubreuil J. Bourahla K. Rahmouni M. Bazureau JP. Hamelin J. Catal. Commun. 2002, 3: 185

Google Scholar
14d Cole AC. Jensen JL. Ntai I. Tran KLT. Weaver KJ. Forbes DC. Davis JH. J. Am. Chem. Soc. 2002, 124: 5962

Google Scholar