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

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ChemCatChem 2014.pdf (905.17 KB)

Publication date

2014-07-02

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Química "Profesor José Carlos Vílchez Martín"

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CIQSO

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https://hdl.handle.net/10272/27613

DOI

10.1002/cctc.201402241

Abstract

The reaction of esters with ethyl diazoacetate catalyzed by the complex [F27–Tp4Bo,3CF2CF3Ag(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.

Keywords

Carbenes; Diazo compounds; Ester functionalization; Silver; Zwitterions

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Bibliographic citation

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

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