Author(s)

Tomoko Mineno^1*, Yuki Suzuki¹, Tomoya Nobuta², Daiki Takano¹, Hisao Kansui³

¹Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan.
²Laboratory of Molecular Design Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan.
³Laboratory of Organic Chemistry, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan.

Protecting groups often play an essential role in organic synthesis, particularly for multi-step synthesis or natural product total synthesis. Various protecting groups areavailable to mask the vulnerable functionality; phenolic hydroxy groups are noteworthy examples, but their stability differs when protected. Herein, the compatibility of protective phenolic functionality was investigated with the implementation of indium (III) triflate-catalyzed oxidative esterification using Oxone in methanol. A wide range of protective moieties was selected and subjected to Oxone-mediated oxidative esterification. For example, sulfonates were found to be sufficiently stable and inert whereas acetals were susceptible to reaction conditions. The details of this investigation are provided.

Compatibility, Protecting Groups, Phenolic Functionality, Oxone, Oxidative Esterification

Mineno, T. , Suzuki, Y. , Nobuta, T. , Takano, D. and Kansui, H. (2022) The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification. Green and Sustainable Chemistry, 12, 83-90. doi: 10.4236/gsc.2022.124007.