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Synfacts 2010(10): 1103-1103  
DOI: 10.1055/s-0030-1258072
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Diclofenac and Lumiracoxib

Contributor(s): Philip Kocienski
T.-S. Mei, D.-H. Wang, J.-Q. Yu*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

Arylacetic acids undergo palladium(II)-catalyzed ortho-C-H iodination in the presence of IOAc generated in situ by reaction of PhI(OAc)2 with iodine. The value of the reaction was illustrated by syntheses of the nonsteroidal anti-inflammatory drugs lumiracoxib and diclo­fenac. A selection of the twenty-three substrates examined shown above illustrates the scope of the reaction. Methoxy-substituted substrates ­react with IOAc non-selectively in the absence of palladium. The reaction must be shielded from light to prevent radical decomposition of acyl ­hypoiodite intermediates.