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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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Publication details

The article was received on 20 Nov 2018, accepted on 06 Dec 2018 and first published on 09 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02899K
Citation: Org. Biomol. Chem., 2019,17, 2110-2115
  • Open access: Creative Commons BY license
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    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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