Download PDF
Synthesis 2011(1): 73-78  
DOI: 10.1055/s-0030-1258332
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Eco-Sustainable Erbium(III) Triflate Catalyzed Formation and Cleavage of tert-Butyl Ethers

Antonio Procopio*a, Paola Costanzoa, Massimo Curinib, Monica Nardic, Manuela Oliverioa, Rosina Paonessaa
a Dipartimento Farmaco-Biologico, Università degli Studi della Magna Græcia Complesso Ninì Barbieri, 88021 Roccelletta di Borgia (CZ), Italy
Fax: +39(0961)36955713; e-Mail: procopio@unicz.it;
b Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia (PG), Italy
c Dipartimento di Chimica, Università della Calabria, Ponte Bucci, 87030 Arcavacata di Rende (CS), Italy
Further Information

Publication History

Received 13 September 2010
Publication Date:
15 November 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

An eco-compatible method, which permits the formation or cleavage of tert-butyl ethers of alcohols and phenols, is proposed. The protection step is performed in solvent-free conditions at room temperature using catalytic amount of Er(OTf)3. The catalyst is easily­ recovered from the aqueous phase and reused several times without significant loss of activity. The deprotection step developed is also highly eco-friendly since the tert-butyl group is removed very quickly from alcohols and phenols in methanol using MW irradiation­.

Key words

green chemistry - Lewis acid - protecting groups - tert-butyl ether - microwave heating

    References

  • 1a Dalpozzo R. De Nino A. Maiuolo L. Procopio A. Tagarelli A. Sindona G. Bartoli G. J. Org. Chem.  2002,  67:  9096 
    Search in Google Scholar
  • 1b Bartoli G. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Procopio A. Tagarelli A. Green Chem.  2004,  6:  191 
    Search in Google Scholar
  • 1c Bartoli G. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Procopio A. Tagarelli A. Eur. J. Org. Chem.  2004,  2176 
  • 1d Procopio A. Dalpozzo R. De Nino A. Maiuolo L. Russo B. Sindona G. Adv. Synth. Catal.  2004,  346:  1465 
    Search in Google Scholar
  • 1e Procopio A. Dalpozzo R. De Nino A. Maiuolo L. Nardi M. Russo B. Adv. Synth. Catal.  2005,  347:  1447 
    Search in Google Scholar
  • 2a Green W. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999. 
    Search in Google Scholar
  • 2b Kocienski PJ. Protecting Groups   Thieme; Stuttgart: 1994. 
  • 3a Bartoli G. Bosco M. Locatelli M. Marcantoni E. Melchiorre P. Sambri L. Org. Lett.  2005,  7:  427 
    Search in Google Scholar
  • 3b Bartoli G. Bosco M. Carlone A. Dalpozzo R. Locatelli M. Melchiorre P. Sambri L. J. Org. Chem.  2006,  71:  9580 
    Search in Google Scholar
  • 4a Kobayashi S. Nagayama S. Busujima T. J. Am. Chem. Soc.  1998,  120:  8287 
    Search in Google Scholar
  • 4b Kobayashi S. Manabe K. Acc. Chem. Res.  2002,  35:  209 
    Search in Google Scholar
  • 5 Dalpozzo R. De Nino A. Nardi M. Procopio A. Mini-Rev. Org. Chem.  2009,  6:  86 
    Search in Google Scholar
  • 6a Lide DR. Handbook of Chemistry and Physics   87th ed.:  CRC Press; Boca Raton: 1998.  p.3-162  
    Search in Google Scholar
  • 6b Parrish CA. Buchwald SL. J. Org. Chem.  2001,  66:  2498 
    Search in Google Scholar
  • 6c Davidson RI. Kropp PJ. J. Org. Chem.  1982,  47:  1904 
    Search in Google Scholar
  • 6d King JF. Lam JYL. Dave V. J. Org. Chem.  1995,  60:  2831 
    Search in Google Scholar
  • 6e Brown HC. Kurek JT. Rei M.-H. Thompson KL. J. Org. Chem.  1984,  49:  2551 
    Search in Google Scholar
  • 7 Pope BM. Sheu S.-J. Stanley RL. Tarbell DS. Friederang AW. J. Org. Chem.  1978,  43:  2410 
    CrossrefSearch in Google Scholar
  • 8 Capello C. Fischer U. Hungerbühler K. Green Chem.  2007,  9:  927 
    CrossrefSearch in Google Scholar