Full Paper

Chemoselective Acylation of Amines in Aqueous Media

  1. Sarala Naik,
  2. Gitalee Bhattacharjya,
  3. Bandana Talukdar,
  4. Bhisma K. Patel

Article first published online: 3 MAR 2004

DOI: 10.1002/ejoc.200300620

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2004, Issue 6, pages 1254–1260, March 2004

Additional Information

How to Cite

Naik, S., Bhattacharjya, G., Talukdar, B. and Patel, B. (2004), Chemoselective Acylation of Amines in Aqueous Media. European Journal of Organic Chemistry, 2004: 1254–1260. doi: 10.1002/ejoc.200300620

Author Information

  1. Indian Institute of Technology, Guwahati, Guwahati 781 039, Assam, India, Fax: (internat.) + 91-3612690762

Publication History

  1. Issue published online: 3 MAR 2004
  2. Article first published online: 3 MAR 2004
  3. Manuscript Received: 3 OCT 2003

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (150K)

Keywords:

  • Amines;
  • Amides;
  • Acylation;
  • Aqueous media;
  • Chemoselectivity

Abstract

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

View Full Article with Supporting Information (HTML) Get PDF (150K)