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Synlett 2001; 2001(12): 1944-1946
DOI: 10.1055/s-2001-18773
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Facile Synthesis of 2-Arylpropenoic Acid Esters by Cross-coupling Using Electrogenerated Highly Reactive Zinc and a Palladium Catalyst

Aishah A. Jalil* , Nobuhito Kurono, Masao Tokuda
  • *Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan; Fax: + 81(11)7066598; E-mail: tokuda@org-mc.eng.hokudai.ac.jp
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Publication Date:
04 December 2001 (online)

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Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. The reaction of this reactive zinc with ethyl 2-bromoacrylate at -20 °C and the following cross-coupling reaction with aryl iodides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 at 70 °C gave the corresponding ethyl 2-arylpropenoates in almost quantitative yields.

cross-coupling - reactive zinc - palladium - electrolysis - α-arylacrylic acids

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