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Domino Catalysis in the Direct Conversion of Carboxylic Acids to Esters

  1. I. Held,
  2. P. von den Hoff,
  3. D. S. Stephenson,
  4. H. Zipse

Article first published online: 24 JUL 2008

DOI: 10.1002/adsc.200800268

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1891–1900, August 4, 2008

Additional Information

How to Cite

Held, I., von den Hoff, P., Stephenson, D. S. and Zipse, H. (2008), Domino Catalysis in the Direct Conversion of Carboxylic Acids to Esters. Adv. Synth. Catal., 350: 1891–1900. doi: 10.1002/adsc.200800268

Author Information

  1. Department Chemie und Biochemie, LMU München, Butenandtstr. 5–13, 81377 München, Germany, Fax: (+49)-89-2180-77738

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Revised: 19 JUN 2008
  4. Manuscript Received: 2 MAY 2008

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Keywords:

  • ab initio calculations;
  • acylation;
  • esterification;
  • nucleophilic catalysis;
  • sterically hindered carboxylates

Abstract

The combined use of high concentration conditions, auxiliary bases, and new catalysts allows for the rapid synthesis of sterically hindered carboxylic acid esters at room temperature. Mechanistic analysis indicates the intermediate formation of acid anhydrides and subsequent rate-limiting transformation to the ester products.

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