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Safe Generation and Direct Use of Diazoesters in Flow Chemistry

Simon T. R. Müller, Daniel Smith, Paul Hellier, Thomas Wirth*

*Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK, Email: wirthcf.ac.uk

S. T. R. Müller, D. Smith, P. Hellier, T. Wirth, Synlett, 2014, 25, 871-875.

DOI: 10.1055/s-0033-1340835 (free Supporting Information)


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Abstract

A safe and fast method for the production of β-hydroxy-α-diazoesters involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. In a three-step sequence, Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters.

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Key Words

addition, aldehydes, diazo compounds, flow chemistry, rhodium


ID: J60-Y2014