Petasis reaction

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The Petasis reaction is a name reaction of organic chemistry , which was named after its discoverer, the Cypriot-US-American chemist Nicos A. Petasis (* 1954). This reaction is a three-component reaction for the synthesis of allylic amines . An amine, a boronic acid and a carbonyl compound are used for this purpose. For this reason, the Petasis reaction is also known as the boronic acid-Mannich reaction .

Overview reaction

The following reaction scheme is intended to illustrate the Petasis reaction for the compounds dimethylamine , trans -propenylboronic acid and formaldehyde :

Petasis reaction

Reaction mechanism

The reaction mechanism of the Petasis reaction is not yet fully understood. Nevertheless, a possible reaction mechanism corresponding to the overview reaction is to be described below.

Reaction mechanism of the Petasis reaction


First, a place addition instead of formaldehyde to the dimethylamine, from the most likely intermediate 1 can be seen. The boron atom of the boronic acid is then attacked nucleophilically by the hydroxyl group of intermediate 1 . After the transfer of the 1-propenyl group , the end product 2 is formed with elimination of boric acid .

Atomic economy

Since boric acid is produced as waste material in stoichiometric amounts in the Petasis reaction , this reaction cannot achieve 100% atom efficiency. However, there are no other waste products, so that the atomic economy of the Petasis reaction can be classified as comparatively good. This applies in particular when the molar mass of the reaction product (and thus also of the reactants ) is large, since the molar mass of the boric acid is less important in this case.

See also

The Petasis reaction is a variant of the Mannich reaction .

Individual evidence

  1. ↑ Nicos A. Petasis; Irini Akritopoulou: The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines . In: Tetrahedron Letters . tape 34 , no. 4 , 1993, p. 583-586 , doi : 10.1016 / s0040-4039 (00) 61625-8 .
  2. ↑ Jie Jack Li: Name reactions: A collection of detailed mechanisms and synthetic applications . 5th ed.Springer, Cham 2014, ISBN 978-3-319-03979-4 , pp. 472-473 , doi : 10.1007 / 978-3-319-03979-4 .
  3. ↑ László Kürti; Barbara Czakó: Strategic applications of named reactions in organic synthesis: background and detailed mechanisms . Elsevier Academic Press, Amsterdam 2005, ISBN 978-0-12-429785-2 , pp. 340-341 .
  4. ↑ Bradford P. Mundy; Michael G. Ellerd; Frank G. Favaloro: Name reactions and reagents in organic synthesis . 2nd ed. Wiley, Hoboken (NJ) 2005, ISBN 0-471-73987-1 , pp. 494 .