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Issue 8, 2019
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Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

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Abstract

Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour.

Graphical abstract: Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

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Article information


Submitted
20 Nov 2018
Accepted
06 Dec 2018
First published
09 Jan 2019

This article is Open Access

Org. Biomol. Chem., 2019,17, 2110-2115
Article type
Paper

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions

W. D. G. Brittain and S. L. Cobb, Org. Biomol. Chem., 2019, 17, 2110
DOI: 10.1039/C8OB02899K

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
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    [Original citation] - Published by The Royal Society of Chemistry.

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