Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O as the Sole Oxidant.

Org Lett

Hefei National Laboratory for Physical Sciences at the Microscale, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China.

Published: December 2021

AI Article Synopsis

  • - The study introduces a new method for isomerizing linear allylic imidic esters using a palladium catalyst and oxygen, which specifically produces β-amino aldehydes.
  • - The process utilizes -butyl nitrite as the only redox cocatalyst to facilitate the reaction.
  • - Butanol (BuOH) is identified as an essential solvent that enhances the yield and specificity of the desired Markovnikov aldehyde products.

Article Abstract

A tandem isomerization--Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. -Butyl nitrite works as a simple, and the only, redox cocatalyst. BuOH proves to be a crucial solvent for achieving excellent yield and specificity toward -Markovnikov aldehyde products.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c03619DOI Listing

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