Passerini Reaction

Aldrich ChemFiles 2006, 6.7, 3.

Aldrich ChemFiles 2006, 6.7, 3.

The Passerini Reaction is another isonitrile-based MCR that yields a-acyloxy carboxamides in a one-pot synthesis from an aldehyde, isonitrile, and carboxylic acid. Of the three components, the carbonyl group is one of the most critical reactants because of the pronounced reactivity of the divalent isonitrile carbon atom towards the C(sp2) electrophilic center.

This reaction can be sluggish with low yields if a strong carboxylic acid or an unusually electrophilic carbonyl compound is not used.1

The traditional Passerini reaction involves an aldehyde in the one pot reaction. In some cases, the aldehydes are not stable or are difficult to handle. Ngouansavanh et al. recently describes substituting the aldehyde with the corresponding alcohol and using 2-Iodoxybenzoic acid (IBX) (3) (661384). This increases the versatility and the number of compounds available using this reaction scheme.2

Scheme 2

3

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Materials

     

References

  1. Xia, Q.; Ganem, B. Org. Let. 2002, 4, 1631–1634.
  2. Ngouansavanh, T. et al. Angew. Chem. Int. Ed. 2006, 45, 3495–3497.

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