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

doi:10.1002/cctc.201402241

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

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 language	English
Pages (from-to)	2206-2210
Journal	ChemCatChem
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/cctc.201402241
Publication status	Published - 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

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title = "Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates",

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. {\textcopyright} 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "carbenes, diazo compounds, ester functionalization, silver, zwitterions",

author = "Riccardo Gava and Fuentes, {M. {\'A}ngeles} and Maria Besora and Belderrain, {Tom{\'a}s R.} and Kane Jacob and Feliu Maseras and Michel Etienne and Ana Caballero and P{\'e}rez, {Pedro J.}",

year = "2014",

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doi = "10.1002/cctc.201402241",

language = "English",

volume = "6",

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Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates. / Gava, Riccardo; Fuentes, M. Ángeles; Besora, Maria; Belderrain, Tomás R.; Jacob, Kane; Maseras, Feliu; Etienne, Michel; Caballero, Ana; Pérez, Pedro J.

In: ChemCatChem, Vol. 6, No. 8, 01.01.2014, p. 2206-2210.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Silver-catalyzed functionalization of esters by carbene transfer: The role of ylide zwitterionic intermediates

AU - Gava, Riccardo

AU - Fuentes, M. Ángeles

AU - Besora, Maria

AU - Belderrain, Tomás R.

AU - Jacob, Kane

AU - Maseras, Feliu

AU - Etienne, Michel

AU - Caballero, Ana

AU - Pérez, Pedro J.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - 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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - 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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - carbenes

KW - diazo compounds

KW - ester functionalization

KW - silver

KW - zwitterions

U2 - 10.1002/cctc.201402241

DO - 10.1002/cctc.201402241

M3 - Article

VL - 6

SP - 2206

EP - 2210

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 8

ER -