Copper(I)-Catalyzed Aerobic Oxidation of α-Diazoesters.

J Org Chem

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.

Published: October 2020

AI Article Synopsis

  • A new method using copper as a catalyst allows for the oxidation of α-diazoesters to α-ketoesters using molecular oxygen.
  • This process works well with both electron-poor and electron-rich aryl α-diazoesters, producing α-ketoesters in good yields.
  • Interestingly, when α-diazo-β-ketoesters are used, they yield α-ketoesters through C-C bond cleavage instead of the expected tricarbonyl products.

Article Abstract

A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.

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Source
http://dx.doi.org/10.1021/acs.joc.0c01744DOI Listing

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