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Passerini Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr479

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Passerini Reaction. Comprehensive Organic Name Reactions and Reagents. 479:2121–2125.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is an atom-economical three-component condensation among isonitrile (i.e., isocyanide), carboxylic acid, and aldehyde (or ketone) to form α-acyloxy amide through acyl rearrangement and tautomerization and is generally known as the Passerini reaction. Several drawbacks of the reaction have been discussed. This reaction has been modified to occur in aqueous solution with obvious advantages of a high reaction rate and easy separation. Lewis acid and Lewis base have been used to promote the Passerini reaction. This reaction has wide applications in combinatorial synthesis.

Keywords:

  • α-acyloxy amide;
  • aryl ketone;
  • aryl isonitriles;
  • Lewis base