Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates

Riccardo Gava, M. Ángeles Fuentes, Maria Besora, Tomás R. Belderrain, Kane Jacob, Feliu Maseras, Michel Etienne, Ana Caballero, Pedro J. Pérez

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13 Citations (Scopus)

Abstract

The reaction of esters with ethyl diazoacetate catalyzed by the complex [F<inf>27</inf>-Tp<sup>4Bo,3CF2CF3</sup>Ag(acetone)] generates α-(acyloxy)acetates in moderate to high yields. This is a novel transformation in the context of carbene-transfer reactions from diazo compounds that, according to experimental and theoretical data, is suggested to occur through zwitterionic intermediates. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)2206-2210
JournalChemCatChem
Volume6
Issue number8
DOIs
Publication statusPublished - 1 Jan 2014

Keywords

  • carbenes
  • diazo compounds
  • ester functionalization
  • silver
  • zwitterions

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    Gava, R., Fuentes, M. Á., Besora, M., Belderrain, T. R., Jacob, K., Maseras, F., Etienne, M., Caballero, A., & Pérez, P. J. (2014). Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates. ChemCatChem, 6(8), 2206-2210. https://doi.org/10.1002/cctc.201402241