TITLE:
The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification
AUTHORS:
Tomoko Mineno, Yuki Suzuki, Tomoya Nobuta, Daiki Takano, Hisao Kansui
KEYWORDS:
Compatibility, Protecting Groups, Phenolic Functionality, Oxone, Oxidative Esterification
JOURNAL NAME:
Green and Sustainable Chemistry,
Vol.12 No.4,
November
11,
2022
ABSTRACT: 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.