Silver‐Catalyzed Functionalization of Esters by Carbene Transfer: The Role of Ylide Zwitterionic Intermediates. Issue 8 (2nd July 2014)

• Record Type: Journal Article
• Authors: Gava, Riccardo; Fuentes, M. Ángeles; Besora, Maria; Belderrain, Tomás R.; Jacob, Kane; Maseras, Feliu; Etienne, Michel; Caballero, Ana; Pérez, Pedro J.
• Is Part Of: ChemCatChem. Volume 6:Issue 8(2014:Aug.)
• Page Start: 2206
• Page End: 2210
• Publication Date: 2014-07-02
• Subjects: Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201402241
• Languages: English
• ISSNs: 1867-3880

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The reaction of esters with ethyl diazoacetate catalyzed by the complex [F₂₇–Tp<inline-formula><alternatives><inline-graphic mimetype="image" xlink:href="ark:/27927/pghwkxqm7m" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /><mml:math altimg="urn:x-wiley:18673880:media:CCTC201402241:tex2gif-sup-1" overflow="scroll" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:msup><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>4 Bo, 3 CF</mml:mtext><mml:msub><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>2</mml:mtext></mml:mrow></mml:msub><mml:mtext>CF</mml:mtext><mml:msub><mml:mtext> </mml:mtext><mml:mrow><mml:mtext>3</mml:mtext></mml:mrow></mml:msub></mml:mrow></mml:msup></mml:math></alternatives></inline-formula>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.</p> </abstract>