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Metal-Free Dehomologative Oxidation of Arylacetic Acids for the Synthesis of Aryl Carboxylic Acids

Hanuman P. Kalmode*, Kamlesh S. Vadagaonkar, Suresh L. Shinde and Atul C. Chaskar*

*Department of Dyestuff Technology, Institute of Chemical Technology, Mumbai 400019, India, Email: hanumankalmodegmail.com, achaskar25gmail.com

H. P. Kalmode, K. S. Vadagaonkar, S. L. Shinde, A. C. Chaskar, J. Org. Chem., 2017, 82, 3781-3786.

DOI: 10.1021/acs.joc.7b00242 (free Supporting Information)


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Abstract

An I2-promoted direct conversion of arylacetic acids into aryl carboxylic acids under metal-free conditions involves decarboxylation followed by an oxidation reaction enabled just by using DMSO as the solvent as well as an oxidant. Notably, aryl carboxylic acids are isolated by simple filtration technique and obtained in good to excellent yields, which makes this protocol applicable for large-scale synthesis.

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proposed mechanism



Key Words

oxidation, oxidative cleavages, iodine, dimethylsulfoxide


ID: J42-Y2017