Download PDF
Synthesis 2014; 46(02): 230-234
DOI: 10.1055/s-0033-1340142
paper
© Georg Thieme Verlag Stuttgart · New York

Solvent-Free, Base-Free Microwave-Mediated Iridium-Catalyzed N-Alkylation of Amides with Alcohols

Tushar D. Apsunde
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Fax: +1(504)2806860   Email: mtrudell@uno.edu
,
Mark L. Trudell*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Fax: +1(504)2806860   Email: mtrudell@uno.edu
› Author Affiliations
Further Information

Publication History

Received: 20 September 2013

Accepted: 17 October 2013

Publication Date:
22 November 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

Solvent-free, base-free microwave-mediated (Cp*IrCl2)2-catalyzed conditions for the N-alkylation of amides with alcohols have been developed. A series of primary and secondary alcohols have been shown to produce high yields of N-alkyl arylamides and N-alkyl alkylamides.

Key words

alcohol - alkylation - amide - iridium

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

  • 1 Greene TW, Wuts PG. M. Greene’s Protective Groups in Organic Synthesis . 4th ed. Wiley; Hoboken: 2007
    Google Scholar
  • 2 Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
    CrossrefPubMed
  • 3 Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
    Crossref
  • 4 Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
    CrossrefPubMed
  • 5 Guillena G, Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2007; 46: 2358
    CrossrefPubMed
  • 6 Guillena G, Ramon DJ, Yus M. Chem. Rev. 2010; 110: 681
    CrossrefPubMed
  • 7 Nixon TD, Whittlesey MK, Williams JM. J. Dalton Trans. 2009; 38: 753
  • 8 Watanbe Y, Ohta TY. Bull. Chem. Soc. Jpn. 1983; 56: 2647
    Crossref
  • 9 Jenner GJ. Mol. Catal. 1989; 55: 241
    Crossref
  • 10 Fujita K, Komatsubara A, Yamaguchi R. Tetrahedron 2009; 65: 3624
    Crossref
  • 11 Liu C, Liao S, Li Q, Feng S, Sun Q, Yu X, Xu Q. J. Org. Chem. 2011; 76: 5759
    CrossrefPubMed
  • 12 Watson AJ. A, Maxwell AC, Williams JM. J. J. Org. Chem. 2011; 76: 2328
    CrossrefPubMed
  • 13 Miao L, DiMaggio S, Shu H, Trudell ML. Org. Lett. 2009; 11: 1579
    CrossrefPubMed
  • 14 Fujita K, Li Z, Ozeki N, Yamaguchi R. Tetrahedron Lett. 2003; 44: 2687
    Crossref
  • 15 Fujita K, Enoki Y, Yamaguchi R. Tetrahedron 2008; 64: 1943
    Crossref
  • 16 Molander GA, Hiebel MA. Org. Lett. 2010; 12: 4876
    CrossrefPubMed
  • 17 Maki T, Ishihara K, Yamamoto H. Org. Lett. 2006; 8: 1431
    CrossrefPubMed
  • 18 Rubio-Perez L, Sharma P, Perez-Flores J, Velasco L, Aries JL, Cabrera A. Tetrahedron 2012; 68: 2342
    Crossref
  • 19 Melsa P, Cajan M, Havlas Z, Mazal C. J. Org. Chem. 2008; 73: 3032
    CrossrefPubMed
  • 20 Kulkarni SS, Hu X, Mantsch R. Synth. Commun. 2013; 49: 1193
    • 21a Ballini R, Bosica G, Fiorini D. Tetrahedron 2003; 59: 1143
      Crossref
    • 21b Hicks JD, Hyde AM, Cuezva AM, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 16720
      CrossrefPubMed
  • 22 Ishihara K, Yano T. Org. Lett. 2004; 6: 198
  • 23 Barbero M, Bazzi S, Cadamuro S, Dughera S. Eur. J. Org. Chem. 2009; 430
  • 24 Han K.-J. Org. Prep. Proced. Int. 2005; 37: 430
  • 25 Al-Musum M, Wai MC, Dunnenberg H. Synth. Commun. 2011; 41: 2888
    Crossref
  • 26 Cho SJ, Roh JS, Sun WS, Kim SH, Park KD. Bioorg. Med. Chem. Lett. 2006; 16: 2682
    CrossrefPubMed
  • 27 Hayashi S, Nair M, Houser DJ, Shechter H. Tetrahedron Lett. 1979; 20: 2961
    Crossref
  • 28 Werry J, Stamm H, Lin PY, Falkenstein R, Gries S, Irngartinger H. Tetrahedron 1989; 45: 5012
  • 29 Zarchi MA. K, Bahadoran A. J. Appl. Sci. 2010; 119: 2345
    • 30a Jiang H, Liu B, Li Y, Wang A, Huang H. Org. Lett. 2011; 13: 1028
      CrossrefPubMed
    • 30b Ritter JJ, Murphy FX. J. Am. Chem. Soc. 1952; 76: 763
  • 31 Jo Y, Ju J, Choe J, Song KH, Lee S. J. Org. Chem. 2009; 74: 6358
    CrossrefPubMed
  • 32 Guna JV, Patel AU, Patoliya VN, Gondaliya SB, Purohit DM. Org. Chem. Indian J. 2012; 1: 151