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Transition-Metal-Free and Chemoselective NaOtBu-O2-Mediated Oxidative Cleavage Reactions of vic-1,2-Diols to Carboxylic Acids and Mechanistic Insight into the Reaction Pathways

Sun Min Kim, Dong Wan Kim and Jung Woon Yang*

*Department of Energy Science, Sungkyunkwan University, Suwon 440-746, Republic of Korea, Email: jwyangskku.edu

S. M. Kim, D. W. Kim, J. W. Yang, Org. Lett., 2014, 16, 2876-2879.

DOI: 10.1021/ol501012f (free Supporting Information)


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Abstract

The use of a NaOtBu-O2 resulted in an efficient oxidative cleavage of vic-1,2-diols to form carboxylic acids in high yields. The present protocol is a green alternative to conventional transition metal based methods. Large-scale production with nonchromatographic purification is also possible.

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Key Words

carboxylic acids, oxygen, green chemistry


ID: J54-Y2014