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Synthesis of the Precursor of Anti-Inflammatory Agents by Cross-Coupling Using Electrogenerated Highly Reactive Zinc

Aishah A. Jalil, Nobuhito Kurono, Masao Tokuda*

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan, Email:

A. A. Jalil, N. Kurono, M. Tokuda, Synthesis, 2002, 2681-2686.

DOI: 10.1055/s-2002-35625


Highly reactive zinc metal was readily 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. This reactive zinc was used for efficient transformation of ethyl 2-bromoacrylate into the corresponding organozinc compound, which was reacted with various aryl iodides in the presence of palladium catalyst to give ethyl 2-arylpropenoates in high yields.

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Key Words

anti-inflammatory agents, Negishi coupling, cross-coupling, reactive zinc, organometallic reagents, electrolysis, electrochemistry

ID: J66-Y2002-1700