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Synlett 2010(2): 253-255  
DOI: 10.1055/s-0029-1219163
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free Iron(III) Chloride Catalyzed O-, S-, and N-Acylation under Mild Conditions

Masatoshi Mihara*, Takeo Nakai, Toshiyuki Iwai, Takatoshi Ito, Toshinobu Ohno, Takumi Mizuno
Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan
Fax: +81(6)69638049; e-Mail: mihara@omtri.city.osaka.jp;
Further Information

Publication History

Received 4 March 2009
Publication Date:
22 December 2009 (online)

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Abstract

An efficient, eco-friendly, and mild method for the acylation of various nucleophiles with acid anhydrides using iron(III) chloride is described. The addition of only 0.1-2 mol% of iron chloride catalyzed the acylation under solvent-free conditions at room temperature to give the acylated products in good yields.

Key words

iron chloride - acylation - solvent-free - alcohols - acid anhydrides

    References and Notes

  • 1a Kumar B. Kumar H. Parmar A. Synth. Commun.  1992,  22:  1087 
    Google Scholar
  • 1b Kumar B. Parmar A. Kumar H. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1994,  33:  698 
    Google Scholar
  • 1c Zhang G.-S. Synth. Commun.  1998,  28:  1159 
    Google Scholar
  • 1d Larock RC. Comprehensive Organic Transformations   2nd ed.:  John Wiley & Sons; New York: 1999.  p.1955 
    Google Scholar
  • 1e Otera J. Esterification   Wiley-VCH; Weinheim: 2003. 
    Google Scholar
  • 1f Greene TW. Wuts PGM. Greene’s Protective Groups in Organic Synthesis   4th ed.:  John Wiley & Sons; New Jersey: 2007.  p.223 
    Google Scholar
  • 2 Baker RH. Bordewell FG. Org. Synth. Coll. Vol. 3   Horning EC. John Wiley & Sons; New York: 1955.  p.141 
    Google Scholar
  • 3 Ishihara K. Kubota M. Kurihara H. Yamamoto H.
    J. Org. Chem.  1996,  61:  4560 
    CrossrefPubMedGoogle Scholar
  • 4 Orita A. Tanahashi C. Kakuda A. Otera J. Angew. Chem. Int. Ed.  2000,  39:  2877 
    CrossrefPubMedGoogle Scholar
  • 5a Chakraborti AK. Gulhane R. Tetrahedron Lett.  2003,  44:  6749 
    Google Scholar
  • 5b Firouzabadi H. Iranpoor N. Nowrouzi F. Amani K. Chem. Commun.  2003,  764 
    Google Scholar
  • 5c Chakraborti AK. Gulhane R. Chem. Commun.  2003,  1896 
    Google Scholar
  • 5d Karimi B. Maleki J. J. Org. Chem.  2003,  68:  4951 
    Google Scholar
  • 5e Chakraborti AK. Gulhane R. Synlett  2004,  627 
    Google Scholar
  • 5f Jeyakumar K. Chand DK. J. Mol. Catal. A: Chem.  2006,  255:  275 
    Google Scholar
  • 5g Chakraborti AK. . J. Org. Chem.  2006,  71:  5785 
    Google Scholar
  • 5h Sakakura A. Kawajiri K. Ohkubo T. Kosugi Y. Ishihara K. J. Am. Chem. Soc.  2007,  129:  14775 
    Google Scholar
  • 5i Kamal A. Khan MNA. Reddy KS. Srikanth YVV. Krishnaji T. Tetrahedron Lett.  2007,  48:  3813 
    Google Scholar
  • 6 White AD. Encyclopedia of Reagents for Organic Synthesis   Vol. 4:  Paquette LA. John Wiley & Sons; Chichester: 1995.  p.2875 
    Google Scholar
  • 7 Chandra KL. Saravanan P. Singh RK. Singh VK. Tetrahedron  2002,  58:  1369 
    CrossrefGoogle Scholar
  • 8 Fieser LF. Fieser M. Reagents for Organic Synthesis   John Wiley & Sons; New York: 1967.  p.392 
    Google Scholar
  • 9 Sharma GVM. Mahalingam AK. Nagarajan M. Ilangovan A. Radhakrishna P. Synlett  1999,  1200 
    Article in Thieme ConnectGoogle Scholar
  • 11 Dalpozzo R. Nino AD. Maiuolo L. Procopio A. Nardi M. Bartoli G. Romeo R. Tetrahedron Lett.  2003,  44:  5621 
    CrossrefGoogle Scholar
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Typical procedure for iron chloride catalyzed acetylation of alcohols under solvent-free conditions: Iron(III) chloride (0.01 mmol) and acetic anhydride (11 mmol) were placed in a test tube and then kept at room temperature for 10 min in air. Alcohol (10 mmol) was added to the mixture, which was then stirred at room temperature. The crude product was purified by silica gel column chromatography to give the desired acetate.