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

Brittain, William D.G.; Cobb, Steven L.

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.

Citation

Brittain, W. D., & Cobb, S. L. (2019). Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions. Organic and Biomolecular Chemistry, 17(8), 2110-2115. https://doi.org/10.1039/c8ob02899k

• Journal Article Type: Article
• Acceptance Date: Dec 6, 2018
• Online Publication Date: Jan 9, 2019
• Publication Date: Feb 28, 2019
• Deposit Date: Jan 11, 2019
• Publicly Available Date: Jan 11, 2019
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 17
• Issue: 8
• Pages: 2110-2115
• DOI: https://doi.org/10.1039/c8ob02899k