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

Aishah A. Jalil; Nobuhito Kurono; Masao Tokuda

doi:10.1055/s-2002-35978

PAPER

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
Fax: +81(11)7066598; e-Mail: tokuda@org-mc.eng.hokudai.ac.jp;

Abstract

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Abstract

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 the corresponding cross-coupling products, ethyl 2-arylpropenoates, in high yields. These cross-coupling reactions were successfully applied to a synthesis of the precursors of non-steroidal anti-inflammatory agents such as ibuprofen, naproxen, ketoprofen, loxoprofen, indoprofen, suprofen, cicloprofen, and flurbiprofen.

Key words

anti-inflammatory agents - cross-coupling - reactive zinc - organometallic reagents - electrolysis

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References

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